Itineraries

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With the fall season settling in, you might already be dreaming of your next European vacation. Look no further— today, we’re rounding up a ‘must-do’ itinerary for your next luxurious vacation from Switzerland to Monaco.

When to Go: Geneva

While there’s certainly never a *bad* time to visit Switzerland or France, the summer and fall months are certainly a favorite. If you’re looking to soak up some sun and spend endless hours on the water, you might opt for June through early September. If you’re comfortable with simply pleasant temperatures (Maybe just a light jacket at night) and fewer crowds, mid-September might be the perfect fit for you.

START HERE: GENEVA

Geneva is quite literally the perfect location to begin your vacation. We recommend a taste of Switzerland before embarking on your journey through France. And, it’s centrally located so you can easily make your way to your next stop: Avignon.

But before we move too fast, let’s break down Geneva.

A popular hub for connections is certainly CDG and if you haven’t traveled through it before, it’s quite honestly what I call…a nightmare. If you have a quick connection time or simply don’t want to wait up to a few hours in line for customs, you might opt for an airport concierge service. Not only will an agent pick you up at your arrival gate, but they’ll help guide you to your next gate. You’ll skip any line, have someone help carry your bags, and safely get you to your gate (or lounge if you have extra time). 

SWITZERLAND | GENEVA

Some definite standouts in Geneva are the Four Seasons Hotel des Bergues and The Ritz-Carlton Hotel de la Paix.

If you’re looking for unmatched elegance with white and gold grand architecture, then we’ve found your match at the Four Seasons Hotel des Bergs. With gorgeous suites, views of Lake Geneva, and a full-service rooftop spa, you’re in for a treat. Walk right outside and you’re just a few minutes walk from Old Town Geneva, the famous Jet d’Eau, and mouth-watering restaurants.   

Lily Pond Luxury Client Perks For Geneva Hotels Mentioned

• $100 USD Hotel Credit

• Daily Breakfast for 2

• Room Upgrade upon arrival, based on availability

Equally as beautiful, but with a more modern, cozy vibe: the Ritz Carlton Hotel de La Paix. With checkered flooring, rolling staircases, and views of the crystal blue Lake Geneva, you’ll be in great hands.

In addition to the beautiful and rather spacious accommodations, is the next-level team. 

Their attention to detail and service makes the stay even more memorable. Greeted with freshly made citrus iced tea and a personalized welcome, you won’t want to leave. Located just one block from the Four Seasons, you can certainly pop over to their restaurant and bar for a lovely drink in a dramatic, gold-encrusted setting. 

You are in Switzerland after all, so calling all cheese lovers… Swiss Fondue is a must!

Les Armures is a popular delight for traditional Swiss cuisine. From fondue and pasta to Swiss onion soup, you won’t be disappointed. 

Seeing Lake Geneva up close is a definite must. Check out the 1-hour public boat tour or rent a boat of your own. And while you’re at it, walk just a few streets over to Old Town Geneva. The shops, restaurants, and bars are quite charming.

Of course, the Swiss are known for their Swiss Chocolate. La Bonbonnière Chocolaterie offers a memorable chocolate-making experience that will most definitely be a stand-out.

And lastly, you can’t go to Geneva without a stop to see the United Nations and Broken Chair statue. 

After a quick train ride to Avignon, we recommend renting a car to explore the region of Provence on your own. 

PROVENCE | AVIGNON

You can use this evening to catch your breath, enjoy a yummy dinner, and relax in your hotel room. Get lost in the quaint town of Avignon, exploring the bakeries, clothing shops, and more. And of course, you can’t forget to see the famous Pont d’Avignon.

The perfect stop for a long afternoon and evening, we recommend staying at La Mirande. A small boutique hotel with just 26 rooms, you’ll certainly feel at home. Every turn features unique prints and marble, sophisticated touches. You’re just steps from the Pope’s Palace with plenty to explore.

Next | Spend the day in L’Isle-sur-la-Sorgue

 From here, you’ll make your way to the countryside. But not without a stop first at one of the most delightful little towns in Provence: L’Isle-sur-la-Sorgue.

Set on the Sorgue River, if you’re lucky enough to hit this town on the weekend, you’ll be enchanted by their weekend markets filled with clothing, antiques, woodwork, and colorful linens—just to name a few. 

You’ll certainly want to stop by Pizzette for a glass of wine, delicious salads, and wood-fired pizzas. And did we mention how adorable their drink menu is? This is the creativity we live for!

After quite a bit of exploring, you’ll be ready to soak in the French countryside with a glass of Rosé.

Next Stop | Terre Blanche 

Terre Blanche is a mixture of luxury, tranquility, and comfort. A resort that is bigger than the whole country of Monaco, you certainly won’t be bored. 

Gorgeous suites and villas await, as does an indoor and outdoor pool, a grand spa, an impressive art collection, and multiple restaurants, and that’s just to name a few! We love their restaurant Le Gaudina for its quintessential Provincial cuisine.

Lily Pond Luxury Client Perks at Terre Blanche

• $85 USD Hotel Credit

• Buffet breakfast for 2 daily

• Room Upgrade upon arrival, based on availability

• Welcome Amenity

• Complimentary Wi-Fi
  
  
  

And did we mention, it was voted the ‘Best Golf Resort Club in Continental Europe’ 3  years in a row?

The concierge is next level, and they’ll assist in arranging perfect experiences for you. Perhaps horseback riding through Villards Stud Farm or visiting the very famous Chateau d’Esclans to try one of the most popular rosés in the world: Whispering Angel.

If you’re up for a day trip to enjoy the gorgeous beach, St. Tropez is only a quick 75-minute drive away. With windy roads, it’s not for the faint of heart, but the views are sure spectacular.  

You’ve probably heard of the famous ‘Le Club 55’ beach club. Be sure to be on the lookout for your celeb sighting from Leonardo DiCaprio to Kate Moss, as it’s where they like to enjoy their summer days.

And once the sun starts to set, you’ll certainly want to go into town, just a few minute’s drive to check out the long line of luxury sailboats, boutiques, artists, and restaurants. 

And for your final destination, the beautiful city of Eze awaits.  

FRENCH RIVIERA: EZE

Hôtel Château de La Chèvre d’Or is renowned for its panoramic views of the Med and a hotel set on top of a cliff. 

It’s quite possibly one of the most unique properties that go above and beyond for its guests. Each room is one of a kind with cozy accommodations.

Now, we can’t fail to mention that with the quirky town of Eze, comes a stair at every step. After exploring the small city, you’ll probably be itching to relax by one of their 2 pools, indulge in a massage, or gaze out into the sea while watching the countless yachts pass by.  

Eze is a great base for visiting the nearby towns like Monte Carlo (Casino anyone?), Villefranche-sur-Mer, Nice, or just a little further, Cannes.

 Let us help arrange a day tour with a top-notch tour guide who will not only show you the best of the best but transport you from stop to stop with a mini history lesson on the side. From the country of Monaco to Villefrance for lunch, with some amazing shopping at Nice. 

And of course, you’ll have to get dressed up to the nines for dinner and a night at the Monte Carlo Casino. For dinner, you’ll want to be sure to grab dinner at Hotel de Paris.

A perfect 10 - 12 days, making your journey from Switzerland to France (or longer, if you wish to relax and linger) will sure to leave you with a permanent smile on your face. From the history, breathtaking views, and kind individuals you’ll come across, you’ll be sure to be itching to visit again soon.

Thank you to designer Abigail Graham, who curated this trip through Switzerland and the South of France. To start the planning process, please reach out to Abigail (abigail@lilypondluxury.com) or your preferred Lily Pond designer!

Itineraries

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Newport, Rhode Island.

The country’s smallest state is big on charm. Rhode Island is more than just historic mansions and sailing – although there are plenty of both to go around. Fun for every age awaits, checking much more than just the boxes on each of the four critical summer vacation “S” factors – sun, sand, sea and scene. 

Easier to access than many New England summer destinations and no less inviting, both Watch Hill and Newport boast fine dining restaurants, championship golf and high-end hotels, as well as the small-town charm that makes both destinations feel like a break from city living. Pick a single spot or combine the two on a weekend or week-long escape with something for everyone in your vacation party.  

Start Here 

We’d begin our trip in Watch Hill, a resort-style escape that offers one plenty of time to sink into vacation mode. 

When selecting a place to bunk down, there’s no better spot than the daffodil-colored Ocean House, which boasts more awards than one can begin to name – a Forbes Five Star designation, membership in Relais & Chateaux, and a reputation as arguably the Northeast’s finest seaside resort. The resort has been hosting well-heeled sun-seekers since 1896, boasting 49 rooms and 15 signature suites that feature luxe touches such as deep-soaking tubs, gratis in-room snacks and afternoon refreshments (we like the malted milk balls). Oh, and did we mention its famous neighbor? Taylor Swift owns the $17 million mansion next door. Ideal for adults seeking a romantic escape but also for families with children of all ages, this hotel fits the bill for nearly any type of traveler. 

Lily Pond Luxury Client Perks:

• Breakfast for two

• $100 one time credit

• Upgrade if available

• Early check-in and late check out as available

Sister property Weekapaug Inn reminds one of family camps of yore. Slightly more rustic (and definitely a bit less pricey) it offers a more secluded marshland location and amenities like an outdoor pool and an in-house naturalist. 

Lily Pond Luxury Client Perks:

• Breakfast for two

• $100 one time credit

• Upgrade if available

• Early check-in and late check out as available

For extended stays, choose Watch Hill Inn, just down the hill from Ocean House proper. Perfect for families or groups traveling together, its condo-style layout offers perks like full kitchens in every room, as well as complimentary continental breakfast, evening wine hours, and reserved parking (a premium in downtown). All properties in the portfolio enjoy reciprocal access, meaning you can stay at one, and dine or use facilities at any. There’s even a fleet of Mercedes house cars happy to shuttle you in-between at your leisure.

How You’ll Spend Your Days

The sleepy town of Watch Hill doesn’t boast overmuch in the way of shopping; the two-street downtown offers a variety of small shops worth browsing for names like Lilly Pulitzer and Vineyard Vines, as well as your usual assortment of tee shirt shops and trinkets. However, a stop at St. Clair Annex for ice cream is a must, as is a visit to the famed Flying Horse Carousel, so dubbed because its ponies fly outward when the carousel is in motion rather than simply bobbing up and down. 

Don’t tax yourself too much, though. Relax on the beach, let the hotel arrange a round of golf, play a game on the championship croquet lawn, or, if the weather doesn’t cooperate, take in a leisurely massage at the hotel’s pampering OH! Spa— the aromatherapy massage with Melissa is among our all-time favorite ways to spend an afternoon. 

Come dinnertime, linger over a farm-to-table meal at COAST, the Ocean House’s fine dining restaurant. Be sure to start with a lemon drop martini on the Verandah. Up for a drive?  Head into town to try Ella’s Fine Food and Drinks, a local favorite, or The Cooked Goose for breakfast and casual fare.  

The morning of your departure, linger over breakfast. The lemon scones in the pastry basket are to die for, and the jazz brunch on Sundays is heavenly. Then, ready yourself for the easy 45-minute jaunt over to Newport. 

Newport Adventure Awaits

Spend your first day in Newport in the Bellevue Avenue Historic District for a look at some of the country’s grandest summer “cottages.” These visits are ideal for adults, but the tours are also suitable for children able to walk and operate a small audio device on their own. We’d suggest at least a three-house pass; you won’t want to stop at just one. Start at The Breakers, the grandest of all residences and former home to the Vanderbilt family. Self-guided audio tours offer interesting tidbits based on personal diaries, oral histories and architectural information. Each of the homes is lovely in its own way, but we’re partial to Rosecliff, which has played a part in movies like the original Great Gatsby and True Lies, as well as The Elms, which boasts a fascinating special tour dedicated just to servant’s life.  

Stay Here 

After an afternoon of house tours, it’s time to check into your hotel. Your choices are numerous. The city boasts dozens of great bed and breakfasts, perfect for a less expensive weekend escape. We love the Lark group of hotels for these, as well as Mill Street Inn. 

Boutique lovers will enjoy the more contemporary vibes at the waterfront Forty 1° North, with its quirky amenities like a giant outdoor chess set, or the intimate Vanderbilt, an Auberge Resorts Collection property, with its well-regarded Dining Room or the gorgeous views from its roof deck bar. 

Lily Pond Luxury Client Perks: 

• Upgrade on arrival, subject to availability

• Full Breakfast daily for two per bedroom

• $100 USD Resort or Hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)

• Early check-in/late checkout, subject to availability

• Complimentary Wi-Fi

But when it comes to luxury, only two hotels are on the list. Downtown’s The Chanler at Cliff Walk is perfectly positioned, as its name suggests, at the start of the three-and-a-half mile long Cliff Walk, a public access walkway that gives you a scenic view of the New England coastline as well as many of the mansions and lavish private homes of Newport. A 19th-century mansion turned hotel, this posh escape feels almost exactly like living in one of the Gilded Age homes it neighbors. Its Cara restaurant is one of our all-time favorite “date night” spots.

Lily Pond Luxury Client Perks:

• Upgrade on arrival, subject to availability

• Continental breakfast for two daily, served in restaurant

• $100 USD Resort/Hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)

• Early check-in/late check-out subject to availability

• Complimentary Wi-Fi

Should you prefer more resort-style accommodations, Castle Hill Inn, a Relais & Chateaux property, is another historic home turned hotel. The property offers some of the area’s best views, including panoramic vistas of Narragansett Bay from nearly every room in the house. 

We’d opt for privacy in one of the luxe beach cottages about 250 yards from the main house.  Sunbathe on “Grace Kelly Beach,” named after the movie star who spent many a weekend in the secluded spot, ride the water taxi into town, or just enjoy cocktails on “The Lawn,” a top destination for guests and locals alike. 

On your second full day in Newport, your opportunities are limited only by your passions. Water lovers won’t want to miss a cruise on 12 Meter Charters’ Heritage, a boat that raced in the 1970 America’s Cup trials. Shoppers can peruse downtown’s many small boutiques, stocking up on everything from preppy essentials to local art, while culture seekers can tour the International Tennis Hall of Fame on Bellevue or play a match at one of the grass courts onsite.  

Getting Here & There 

It’s easy to get to Rhode Island from virtually any spot in the Mid-Atlantic, with many cities offering direct flights into Providence, or connect via train from Boston or New York. While both towns are mostly walkable, if you’re visiting for longer than a weekend, we’d suggest renting a car. It makes getting between the mansions and downtown much faster. If you’d prefer to take your chances with cabs, Newport does have a small Uber presence. 

When to Visit 

As with most seaside towns, high season runs from Memorial Day through Labor Day. Expect high volumes of tourists, particularly during holiday weekends and big events like late July’s Newport Antiques Show. Of course, you’ll also get the best weather. We are partial to mid to late June, when days can be crisp and clear in the 70s, and nights require a light jacket or sweater—the water isn’t yet warm enough for swimming, and so crowds are slightly smaller than in July or August. Westerley, where Ocean House is located, basically shutters before and after the holidays, so expect your trip to be limited to just the resort and its amenities if you plan a fall visit, although we do enjoy the off-season for fewer crowds and better than average rates. 

Itineraries

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Flora Farms

A perennial favorite for West Coast travelers and sleeper hit for East and Mid-Coasters, Los Cabos never disappoints. Boasting more luxury hotel options than almost any place in North America, top-notch dining, more than 350 days a year of sunshine and direct flights from many major cities, there’s no wonder why travelers flock to Cabo again and again. 

Today, we’ll round up some of our top choices, sharing details on new hotspots and old favorites alike, plus some of our favorite ways to make the most of your week or long weekend in paradise. 

When to Go 

It’s hard to choose a bad time to visit Cabo San Lucas. High season runs from December through April, but anytime from early November through May is comfortable – try these shoulder months, even into mid-June, for a more reasonable room rate and something less than scorching temperatures. 

When possible, we’d avoid late August through October, which are known to have near triple-digit temps, humidity and have the highest chance of rain.  

Stay Here 

Unlike many resort destinations, Cabo lacks one definitive high-end favorite. We like each of the area’s leading hotels for different reasons. At each, you’ll find a level of luxury where staff anticipates needs practically before you think of them. Enjoy WiFi service in Cadillac and Mercedes house cars that shuttle guests to and from the airport, on-demand foot massages and cooling Evian misters by the pool and in-room sewing kids customized to the color of your wardrobe. It’s practically guaranteed that you’ll come home missing your retinue of staff –  after all, they outnumber guests at most resorts nearly five to one. 

Finding your perfect Los Cabos resort is a bit like finding your perfect date – there are options for every mood. Our designers can pair you with the ideal spot for your unique needs – reach out today to ask for our assistance!  

The Old Guard: 

Don’t care if you leave the resort? In Los Cabos, halfway between Cabo San Lucas and Cabo San Jose, you’ll find plenty of luxury in “the corridor.” 

It’s no secret that the area’s most exclusive resort is also its oldest, celebrating its 18th anniversary this year. There’s no signage, just a single white wall with a massive gate that marks the entrance to Rosewood Las Ventanas al Paraiso, which translates literally to “The Windows to Paradise.” This quietly luxurious resort caters to the ultra-wealthy, although every guest feels pampered, almost cosseted. Staffers know returning guests by name, pointing out that they see most families year after year, or month after month – one family recently celebrated their 30th visit to the resort, and private butlers prep tasteful amenities like sewing kits customized to the colors packed in your luggage. 

While all rooms are lovely, if you can, opt for a rooftop suite or for one of the 12 beachfront private villas, which start at more than 4,500 square feet and offer amenities like private massage rooms, indoor-outdoor living and dedicated butlers who make breakfast en casa each morning using local ingredients sourced from nearby farms. 

Equally lovely, but with a bit more pizazz is the newer Montage Los Cabos, opened in late 2018. Boasting one of the few swimmable beaches in Cabo and abutting the luxurious Twin Dolphin golf course and Maravilla residential community, the 122 room and 52 residence resort offers sleek and modern Cabo luxury and some of the area’s best service. All rooms offer views out over Santa Maria Bay, and access to amenities including an oversized spa and fitness center, the gorgeous Marea restaurant, and of course, the aforementioned swimmable beach. We particularly love their oversized multi bedroom residences, perfect for families. 

Another popular choice in the corridor is the area’s only Relais & Chateaux property, Auberge resort Esperanza. The resort boasts tasteful decor in a soft neutral grey and blue tones and 57 well-appointed rooms, many with outdoor plunge Jacuzzis or hammocks for enjoying a late afternoon breeze. One of our favorite spots, Esperanza boasts one of the best resort boutiques and one of the area’s most romantic restaurants, Cocina del Mar, known for its crashing waves and sunset views. 

By day, sprawl out in palapa-roofed guest suites or get your tan on new in-water chaise lounges and private cabanas available for day rentals. Staying with a group? The resort’s private villas, which boast three to four bedrooms, are often available for extended rentals as well. (We also often source larger homes within this area for groups, just inquire with your advisor for private home rental choices in Cabo and beyond.) 

It also offers one of our favorite spas, a palapa-topped area where all treatments take place in private garden-style suites and guests are pampered with custom local juices, dubbed “Agua Frescas” pre- and post-treatment. 

Sister hotel Chileno Bay boasts a swimmable beach, top notch spa and even wellness rooms with optional Peloton bikes, as well as buzzy restaurant Comal.

The younger crowd on a girlfriend getaway or those who crave proximity to in-town nightlife should opt for the 96-room Waldorf-Astoria Los Cabos - Pedregal. 

Avoiding the paparazzi? Built into the side of Pedregal Mountain and on a private, horseshoe-shaped beach, the resort is accessible only by a nearly 1,000-foot-long private tunnel. We love that even base-level rooms here are all ocean-view and spacious, starting at more than 850 square feet with terraces and private plunge pools.  Book the beachfront casitas for extra privacy (you’ll get your own roped off area of beach and access to a private pool right from your shower) or the corner Estrella Suites, with their outdoor fire pits, for the best sunrise and sunset views. Families will like the multi-bedroom residences and the dedicated kid’s pool. 

You’ll find many of the amenities much the same – spend days by the infinity pool, noshing on fresh sea bass ceviche at the Crudo Bar, or in the luxe Luna y Mar Spa, an oasis with 10 private treatment rooms situated in overwater private cabanas. Don’t miss sunset drinks at their Champagne Terrace, which offers more than 15 kinds of by-the-glass bubbly. From there decide if you prefer seafood at the cliffside El Farrallon or the hacienda-inspired Don Manuel’s. If it was good enough for George and Amal on a recent visit … we’re pretty sure you’ll like it too.  

Another old guard gem is One & Only Palmilla. The area’s largest luxury hotel at 173 rooms, guests of this resort may feel as if they’re in the Caribbean, not Mexico, thanks to its lush landscaping, a departure from other properties that go for a more desert-chic appeal. 

We love their signature restaurant, SEARED by Jean-Georges Vongericheten, (get the to-die-for short rib paired with an excellent selection of Mexican wines) as well as their spa, which offers a blowout bar as part of the salon as well. 

We love that this resort offers the most luxury goods – its boutique, Neo, stocks made-for-the-resort collections by names like Melissa Obadash, Stella McCartney, and Christian Louboutin, and its guests are the most likely to head to dinner in sky-high heels and their hair perfectly coiffed. 

The New Delights: 

Within the past few years, a number of noteworthy options have emerged, including Zadun, a Ritz-Carlton Reserve, the first Reserve property in Mexico. Rooms offer panoramic ocean views and many feature plunge pools.

The East Cape has also emerged as a strong option for guests seeking relaxation away from the crowds. Four Seasons Los Cabos offers swimmable beaches, a marina, and oversized rooms perfect for families. We’d caution, however, that Four Seasons is a destination unto itself – part of a larger complex of properties still under development, including an Aman resort – and also and hour plus drive from options in Cabo San Lucas. 

Up the coast just a bit in the hip neighborhood of Todos Santos, Paradero is a great choice for those seeking wellness inspired accommodations. 

Chic Boutique: 

There are several other worthy options as well – offering style at a lower price point than the options above. For a buzzy vibe, we love The Cape, part of Hyatt’s Thompson hotel brand. It boasts a rooftop bar and arch views from each room. It’s also right on Monuments Beach, the perfect place to catch prime surfing waves. We also love the buzzy Nobu hotel, which offers the famed restaurant by the same name as well as LA favorite Malibu Farm, and the newer Viceroy Los Cabos. 

If you prefer all-inclusive, the Leading Hotels of the World member Marquis Los Cabos has been re-branded an adults-only escape. For more funky, laid-back vibes, try Hotel El Ganzo (“The Goose”) in San Jose Los Cabos. The boutique hotel boasts a recording studio in the basement! 

Where to Eat & Drink

While you’ll certainly enjoy your fill of tacos and guacamole, Los Cabos is known as much for its fine dining as it is for its tequila tastings. Speaking of tequila, don’t miss the chance to do a tasting of Mexico’s signature spirit – most resorts can arrange a class for a nominal fee. You’ll learn the difference between the newest – blanco and the most aged – anejo – as well as what varieties are best for sipping and which should be mixed into margaritas. 

While resort food can get pricey, each of the luxury resorts offers its own signature dining experience – be sure to pop around and taste test. Freshly-caught fish, like local dorado or sea bass, is always a perfect choice. 

Speaking of fresh, don’t miss the farm-to-table favorite Flora Farms, a 10-acre working farm and event venue in the foothills of the Sierra de la Laguna Mountains in Los Cabos, Mexico. Have an afternoon? Try a cooking class followed by dinner at Flora’s Field Kitchen. Brunch is also popular. We also suggest an evening at Acre, which offers similar farm-to-table fare and a fantastic boutique. Flora offers a fantastic boutique spa, and Acre even has a few intimate overnight accommodations if desired. 

In town, Hacienda Cocina and Cantina is a perennial favorite, offering gorgeous sunset vistas with views of “El Arco,” the famous rock formation arch at Land’s End. Edith’s is another favorite, offering Mexican classics with a seafood focus and and a convivial atmosphere. It’s sister restaurant, The Office, is right on the sand and popular with groups. 

Where to Play

If you can motivate yourself to get up from your lounge chair, you won’t be disappointed. 

Cabo boasts the usual array of resort-destination activities, most of which haven’t changed in recent years – from beachfront horseback riding to parasailing – with something for every price point and level of adventure. Let your resort do the booking – most get preferred rates. 

Golfers will love world-class courses by designers like Tom Fazio and Tiger Woods. Choose from scenic desert settings to spectacular ocean vistas. Just take an early tee time – the midday sun here could challenge even the most dedicated links-goer. 

Water enthusiasts can get their fill in a variety of ways. Most resort beaches aren’t swimmable thanks to crashing waves and heavy undertow, so instead charter a boat (like the Buccaneer Queen, shaped like a pirate ship, ideal for kids)– or hire out a sport fishing charter for a day-long or half-day excursion to catch Marlin, Swordfish, Dorado and more. Most resorts will even prepare your catch fresh for dinner that evening! 

More of the sightseeing variety? From December through April, book a whale-watching tour. It’s a memorable sight; thousands of whales frolic and mate in the warm Cabo waters each year. 

Should you find a rare day of rain or just want to get out of the sun for awhile, stroll the town of Cabo San Lucas and make a stop at Luxury Avenue, which offers brand names like Carolina Herrera, Salvatore Ferragamo, Coach, Fendi, Cartier, Chopard and more. For a more authentic feel, make the 30-minute trip to neighboring Cabo San Jose. If you can, go on Thursday evenings, where all of the areas small galleries open their doors and offer welcome music and cocktails for a local art walk. You’ll find everything from handmade embroidered chemises to Mexican fire opals. Bartering is expected, so don’t be afraid to negotiate (politely, of course) for the best price. We also love La Coyota, a fun shop for souvenirs and keepsakes from the same ownership team as Edith’s and The Office.

Of course, there’s always the option to lounge by the pool and let your butler bring you fresh fruit, cool towels, and an icy margarita. We won’t judge. 

What to Know (Before You Go)

Don’t let talk that Mexico isn’t safe fool you – Cabo San Lucas is an exception to the rule. Located on the very tip of the Baja California peninsula, the area, which boasts 20,000 American citizens as part of its 200,000-person population, is located practically on its own private oasis. Even nearby towns like the artsy village of Todos Santos are safe. Of course, that doesn’t mean wander around alone at night – this popular “spring break” destination is much like any other major city. 

Because of Cabo’s popularity with L.A. and New York visitors, the resorts and nightlife are trendier than most Caribbean escapes, so pack your finest caftans and bangles for poolside lounging and nighttime adventures – and don’t be surprised to see a line of private jets on the tarmac when you arrive. 

Speaking of those adventures – we’d arrange private resort transportation and avoid the cabs. Drivers make Manhattan taxi rides seem tame, and pricing can be a bit of a hustle. A firm “no, gracias” will do. It’s about a 30-minute ride from the airport to most resorts. Most luxury resorts offer private transfers in chauffeured vans and SUVs in package pricing, with some even helping fast track you through security on the return. Speaking of, opt for a ticket (about $30) to the VIP lounge at the airport to enjoy free Wi-Fi, snacks and more.  

In terms of scenery, you’ll find that most of the area looks much like it did pre hurricane, albeit newer and fresher. Cabo is a desert oasis, so most resorts opt for a more austere approach, letting the crashing waves of the Sea of Cortez and the Pacific Ocean do the talking. Many resort-front beaches aren’t swimmable, but perfect for lounging and strolling. 

Your biggest problem? Once you’ve gotten used to the Cabo lifestyle, you probably won’t want to return to the real world.   

For specific questions about Cabo, home rentals, or other VIP experiences, reach out to your Lily Pond Luxury Designer. 

Itineraries

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Casa Palmero, Pebble Beach Resort.

Pebble Beach. The American Club. Kiawah. These names evoke curving fairways, breathtaking views, and challenging water holes. But today’s luxury traveler isn’t just seeking the greatest 18 holes, they’re looking to experience a memory to last a lifetime. 

Today’s innovative hotel and resort destinations ensure that while amenities like golf, tennis and wellness may still be a prime draw, the accommodations, dining and level of service match with the Five Star name.

Today’s Active Traveler Is Different

For some, this may mean once-in-a-lifetime experiences on Pinehurst’s Number Two or hitting a backhand with instructors who teach the pros, while for others, that may mean a guided morning hike in Sedona’s Red Rocks, a cycling trip through France or a holistic spa experience at a destination wellness resort. 

No matter the activity, the data has shown that today’s luxury traveler is more discerning than ever before. No longer is it enough to merely travel to the latest, off-the-beaten-path destinations; personalized travel is the new “luxury.”  Experiences have to go deeper and appeal to personal interests. Tailor-made excursions continue to become de rigueur.  Travel must also address certain desires – including meeting the needs of any non-golfers or tennis players in the family.  

We’ve done the legwork for you, rounding up 12 (we couldn’t narrow it any further!) of the country’s most incredible resorts where active travelers can relax and kick back in style. 

Kiawah Island, South Carolina

Just 45 minutes from the burgeoning hipster paradise of Charleston, South Carolina sits the endless sunshine of Kiawah Island Golf Resort, one of the country’s best places for golf and tennis lovers. Stay at The Sanctuary at Kiawah Island, an intimate resort resembling an old Southern estate, where you’ll relax in the elegant spa or fine dining restaurant after a day spent practicing your backhand on one of 19 Har-Tru clay courts or five hard courts, as well as a practice court featuring a ball machine and automated retrieval system. The resort offers regular women’s tennis weekend programs, stroke-a-day clinics, drill sessions, mini camps and more. Prefer the links? You’ll find more than 90 holes of championship golf, designed by major names like Jack Nicklaus, Tom Fazio and Gary Player. Our favorite? The Pete Dye-designed Ocean Course, one of only four courses in the U.S. to have hosted every major PGA event in the country. It boasts spectacular views of the Atlantic Coastline from every hole. 

Clients also love the many private home options available here. Book early to secure oceanfront or “Premier” homes, many of which boast pools as well. There are also economical condo and villa-style accommodations. Lily Pond Luxury clients also enjoy upgrade on arrival, subject to availability, daily full breakfast for two guests per bedroom, a $100 USD Resort/Hotel credit to be utilized during your stay (not combinable, not valid on room rate, no cash value if not redeemed in full), early check-in/late check-out subject to availability, complimentary Wi-Fi, and a full bottle of sparkling wine from the honor bar as a welcome amenity.

Monterey, California 

With an Oceanside setting this pristine, it’s almost believable that championship golf is a secondary perk. Casa Palmero, part of Pebble Beach Resort, offers just 24 Mediterranian-style rooms overlooking the first and second fairways of the Pebble Beach links. 

Perks for Lily Pond Luxury clients include:

• Upgrade on arrival subject to availability, a Continental Breakfast Basket delivered to your room daily

• $100 USD resort credit to be utilized during your stay (which can be used on retail, spa, food & beverage and golf at The Links at Spanish Bay or Del Monte Golf Course - the credit cannot be used on Spyglass Hill Golf Course or Pebble Beach Golf Links, and it is not combinable, not valid on the room rate, and has no cash value if not redeemed in full)

• Early check-in/late check-out subject to availability

• Complimentary Wi-Fi

Another favorite? The romantic Inn at Spanish Bay, with its evening bagpiper who plays along the cliffs as the sun sets. But the real highlight are the five courses, from the famed Pebble Beach Golf Links, rated America’s #1 public golf course by Golf Digest, to the challenging Spyglass Hill or The Links at Spanish Bay, a unique Scottish-style experience.  

Kohler, Wisconsin

It’s hard to believe, but two-and-a-half hours from Chicago and one hour from Milwaukee sits one of the country’s finest five-star hotels and golf escapes – The American Club. Located on the grounds of the Kohler campus in an English Tudor-style mansion, the luxury resort that was once a dormitory for Kohler workers is now a peaceful retreat (with spa-like bathrooms full of Kohler products, naturally). Take advantage of the onsite Kohler Academy Golf School, which offers a unique JC Video System to monitor your swing, as well as one-, two-, three- and four-day programs designed to cater to your individual game. When you’re ready to hit the links, take advantage of four Pete Dye-designed courses, plus a regular tournament series designed to cater to the competitive among us.  This area is particularly popular this year, thanks to the Ryder Cup tournament, which will be held in Wisconsin nearby at Whistling Straits. 

Cape Cod, Massachusetts 

Many equate the Cape with preppy yachting parties, lobster bakes and beaches, but it’s also home to some of the country’s best golf, thanks to the area’s only Nicklaus Design golf course at Ocean Edge Resort & Golf Club. It’s perfect for new and experienced golfers alike, with its onsite golf Academy, as well as nightly events like ‘Wednesday Women’s Workshop,’ ‘Monday & Wednesday Night Pee Wee Golf,’ and ‘Friday Night Fun.’  Tennis aficionados won’t be disappointed either – the resort also offers fundamental group classes, on-court workouts and ample programming for adults and kids alike. There’s also a tennis happy hour, perfect for socializing after a long day on the court. Opt for rooms at The Mansion at Ocean Edge, adjacent to the historic Victorian-style Nickerson Mansion, the most elegant of the resort’s accommodations. Many guests also prefer to stay just on the ocean side of the Cape, at Chatham Bars Inn, which offers an attractive mid of cottage and resort-style accommodations, about 20 minutes away.  

Lily Pond Luxury Client Perks:

• Upgrade on arrival, subject to availability

• Daily in-restaurant breakfast for two guests per bedroom

• $100 USD equivalent Spa Services credit to be utilized during stay (not combinable, no cash value if not redeemed in full)

• Early check-in / late check-out subject to availability

• Complimentary Wi-Fi.

Half Moon Bay, California

Just north of San Francisco, discover the impeccable Ritz-Carlton, Half Moon Bay, an intimate escape perched high above the Pacific Ocean. For a once-in-a-lifetime experience, try The Legends Golf package, which features unlimited play on the Old Course, Arnold Palmer’s classic American parkland-style course, and the Ocean Course, a Scottish-links-style designed by Arthur Hills. The package also includes overnight accommodations in a coastal view guestroom, unlimited same-day replays for one or two players, use of a golf cart, warm-up range balls, bottled water, access to locker rooms, and a golf-themed amenity. Prefer tennis? Try one of six courts for daily clinics, doubles mixers or private lessons. 

Lily Pond Luxury Clients Perks:

• Upgrade on arrival, subject to availability

• Daily full breakfast in the Conservatory Restaurant for up to two guests per bedroom

• $100 USD equivalent in Resort or Hotel credit to be utilized during your stay (excluding alcohol, taxes, gratuities and cannot be used in Spa, retail or 3rd party entities, nor applied toward room rate, tax or valet parking - it has no cash value if not utilized during dates of stay)

• Early check-in/late check-out subject to availability

• Complimentary Wi-Fi

Pinehurst, North Carolina

Dubbed “The Cradle of American Golf,” Pinehurst Resort, with its three hotels, condos and eight 18-hole courses, was once a true golfer’s retreat. But recent renovations have left its southern charm – like the Carolina Room, where diners still dress in blazers to come to elegant multi-course dinners and watch ballroom dancing – but also given it modern upgrades, like a 31,000-square-foot spa with 28 treatment rooms. While the 31 miles of golf, the largest number of golf holes in the world at a single golf resort, remains the main draw, tennis lovers will also find something to smile about, thanks to expert instruction and 16 clay courts. A visit to Pinehurst feels like a step back in another era, thanks to touches like elegant afternoon tea served in the lobby and vintage photographs that dot the halls showing well-heeled guests from the resort’s more than 125+ year history, but one with a luxurious touch. 

Las Vegas, Nevada

Las Vegas may feel like an odd choice to welcome one of the country’s top golf retreats, but it’s precisely the reason why so many top links players love the 18-hole, par-70 course at Wynn Las Vegas. It’s a challenging Tom Fazio-designed course (recently updated from the 2005 original after a several-year hiatus) and the only one available attached to a resort on the strip, letting you go from blackjack table to tee box without ever leaving the resort. Of course, some of the country’s top courses, like Shadow Creek, are also nearby, so you’ll likely want to golf several times during your stay. And, of course, there’s plenty to do at night, from award-winning Cirque show La Reve to world-class shopping by names like Louis Vuitton, Chanel and Graff to the five-star spa to dozens of upscale restaurants – including the top-notch SW Steakhouse and the new Delilah, a fun supper club concept. We prefer the Tower Suites at both Wynn and Encore, which offer private check-in and entrances, as well as larger villas that are ideal for groups.  

Perks for Lily Pond Luxury Clients include: 

• Upgrade on arrival to the next room category, subject to availability

• Daily Breakfast Credit of $30 per person, for up to two guests per bedroom (to be utilized in Tableau, The Drugstore, Jardin, Goodies on Demand, Tower Suites Lobby Bar. Excludes in-room dining)

• $50 Spa Credit and $50 Food and Beverage Credit, once per stay.

• Early check-in and late check-out, subject to availability

• Complimentary Wi-Fi

Palm Beach, Florida

It’s no surprise that our travelers love Florida – and particularly Palm Beach – for its warm weather fun. While there are many courses and courts to hit in the area, guests return to iconic property The Breakers time and again to enjoy the resort’s two courses as well as onsite John Webster Golf Academy, and also the 10 Har-Tru tennis courts and top-notch instruction. Pair this with an afternoon at a poolside cabana or shopping on Worth Avenue and you have a trip worthy of the athletes (both the sport and shopping kind) in the family. 

Perks for Lily Pond Luxury Clients include:

• Upgrade on arrival, subject to availability

• Signature breakfast daily for two guests per bedroom served in The Circle or The Beach Club Restaurant

• $100 USD Resort/Hotel credit to be utilized during stay (cannot be transferred between reservations, not combinable, not valid on room rate or for gift cards, no cash value if not redeemed in full)

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

For many dates this year, we are also able to secure a 6th night free for guests. Inquire about your preferred dates today!

Miami, Florida

When it’s backed by a name like Donald Trump, you know that the amenities at Trump National Doral® are going to be over the top. The Trump Organization recently put more than $250 million into the property to complete a dramatic renovation of the historic 800-acre resort. This included a total rooms overhaul, plus updating the four championship golf courses like the signature “Blue Monster”, adding a new clubhouse and new spa facility. Take advantage of the onsite Jim McLean Golf School, get fit for new clubs with True Spec Golf’s expert fitters and more than 30,000 combinations of club heads and shafts in stock, or plan a zen-out weekend in new spa suites, featuring serene accommodations with Spanish Revival details in a villa-like setting just steps from the main clubhouse. You’ll also enjoy high-end dining from names like BLT Prime, an upscale steakhouse, as well as services of the Trump Card, where you’ll enjoy personalized attaché services, one-of-a-kind experiences and more. 

San Diego, California 

Spanning 45 acres of lush gardens, trails and olive groves, Rancho Valencia, a Relais & Chateaux resort just outside of San Diego, offers a well-appointed escape for those seeking an active and healthy lifestyle. Fresh from a $30 million renovation, the property has 18 recently resurfaced plexi-pave championship tennis courts and an expanded spa and fitness center, with a 1,000-square-foot Serenity Yoga Pavilion that now hosts numerous Yoga sessions, fitness classes, exercise programs and retreats hosted by top-tier fitness and wellness professionals. We love the active influence of this luxury resort, where all classes are complimentary and end with a fresh cold-pressed juice or protein shake. Plus, the resort’s all-suite casita-style accommodations make you feel as if you’re in a well-appointed private home, albeit one with Frette terry robes, Illy espresso machines and perhaps a private plunge pool.  

Perks for Lily Pond Luxury Clients include:

• Upgrade on arrival, subject to availability

• Daily full breakfast for two guests per bedroom (maximum $40 credit per person)

• $100 USD Resort or Hotel credit, (Not valid in Sheridan, the resort's boutique. Not combinable, not valid on room rate, no cash value if not redeemed in full)

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

Irving, Texas

Just moments from Dallas and Fort Worth proper sits a go-to resort for well-heeled Texans and visitors alike, the Four Seasons Resort and Club Dallas at Las Colinas. Following the “everything is bigger in Texas” motto, the resort boasts a 176,000-square-foot sports club, four indoor and eight outdoor tennis courts, a saltwater lap pool, squash and racquetball courts and a running track. One of our favorite options? The early bird challenge – starting at 6 AM – which means you can get in a Tennis match before a day of shopping – may we suggest a visit to the original Neiman Marcus? Of course, golfers will enjoy their fill too, thanks to two courses, the famed TPC Four Seasons Las Colinas, home to the annual AT&T Byron Nelson, as well as the exclusive Cottonwood Valley, available only to guests and members of The Sports Club at Four Seasons, with its bunker shaped like Oklahoma and lake resembling the Gulf of Mexico. 

Perks for Lily Pond Luxury Clients include:

• Upgrade on arrival, subject to availability

• Daily continental breakfast for two guests per bedroom, in-restaurant (excludes Sunday Brunch) or via room service

• $100 Resort/Hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full, excludes pro shop or gift shop purchases)

• Early Check-In / Late Check-Out, subject to availability

• Complimentary Wi-Fi

For some 2022 dates, we have a third-night-free package for guests.

Lanai, Hawaii

Let’s face it, when presented with the natural splendor that is Hawaii and its many islands, it’s easy to see that golf and outdoor pursuits could become an afterthought. But the seven-island chain is known for some of the country’s most challenging and enticing links. One of our favorites? Four Seasons Resort Lanai is fresh from multi-million-dollar renovation done to the owner and Oracle CEO Larry Ellison’s exacting standards and posh perks a NOBU restaurant. Just off the coast of Maui, this intimate island is a romantic retreat, but it also boasts Hawaii’s #2 rated golf experience the Jack Nicklaus-designed Manele Golf Course, which boasts dramatic ocean views from every hole (and frequent whale sightings from the fairways) as well as a challenging five-tee concept with first shots taking place over natural gorges and ravines. Take in expert instruction with Trackman swing analyzers before booking an unlimited golf package for two or just enjoying a leisurely sunset nine-hole round. 

Lily Pond Luxury Perks include:

• Upgrade (one category only) on arrival, subject to availability (applicable to standard room categories only, excludes specialty suites)

• Daily Continental breakfast for two guests served in the restaurant (Daily $48.00 USD breakfast credit for two, per bedroom)

• $100 USD equivalent Resort or Hotel credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)

• Welcome Amenity

• Complimentary Wi-Fi

For some 2022 dates, we can also offer 5th-night-free packages, and extra resort credit offers.

Itineraries

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Dorado Beach, a Ritz-Carlton Reserve.

The Caribbean’s Easiest Escape Awaits 

Dubbed “the gateway to the Caribbean” for its large cruise ship and air presence, the 110-mile long and 35-mile wide island of Puerto Rico has much more than just beaches to offer guests. Luxury shopping, resorts for every style of traveler, world-class golf, and nature activities galore offer something for families and couples alike. 

Stay Here

Deciding on what “type” of vacation you’d like to have may be the hardest decision you make during your entire visit to this friendly island. As islands go, Puerto Rico is large, and  you’ll likely start and end your journey in historic San Juan, the capital.

Sadly the Ritz-Carlton has been closed since the last Hurricane, but we like the well-located 

Condado Vanderbilt Hotel, which is full of gorgeous Spanish Revival architecture. We love the Commodore’s Suites— these corner suites have two balconies and massive living spaces, perfect for multi-generational travel.  You also won’t want to miss the new taco and tequila bar, a more casual dining option than the popular onsite 1919, where chef Juan Jose Cuevas, who came from a background of three- and four-Michelin star restaurants, puts farm-to-fork cuisine at the forefront.  The spa is also a must-visit – it boasts the only hammam in Puerto Rico. The neighborhood is also a great one to experience the local culture. 

Fans of boutique properties will love Hotel El Convento, a Small Luxury Hotels of the World property built inside a three-centuries-old Carmelite Convent, with its marble chessboard floors and mahogany furniture. 

The adults-only O:live Boutique Hotel, another Small Luxury Hotels of the World property, is perfect for couples with its intimate, 15 room size and trendy Sage Steak Loft restaurant. Be aware – the see-through glass showers aren’t for the modest, and rooms, while impeccably designed, can be on the small side. 

Were it up to us, we’d split our time between Condado and a more remote resort destination – we love St. Regis Bahia Beach Resort along the island’s Eastern coast, perfectly poised between El Yunque National Forest and bordering the 5,000-acre Espíritu Santo River State Preserve. This eco-retreat blends signature St. Regis service (it’s the only hotel from the brand in the Caribbean) and perks like nightly champagne sabering and a Jean-Georges Vongerichten restaurant, Fern, with laid back Caribbean charm. Relax in the Remède Spa (the private gardens are fab) or get active on the 18-hole Robert Trent Jones, Jr. golf course. 

However, there’s no doubt that the island’s top property is Dorado Beach, a Ritz-Carlton Reserve.  The world’s first Ritz-Carlton Reserve branded residences and first Ritz-Carlton Reserve hotel to open in the Americas is the island’s top resort, pampering without being showy. You’ll never need to leave, either – three restaurants, golf, water park, tennis, and the top-notch Spa Botánico (relax in the purifications gardens) provide all the amenities you’ll need. Choose between oversized residences and well-appointed hotel rooms and suites, many with private plunge pools, split between East and West Beach locations. Broadly, the West Beach is more coveted given its location, but many clients prefer East due to the added privacy and more quiet feel. For longer stays, book a multi-bedroom residence or the 5 bedroom Su Casa, a 1920s hacienda-style villa originally built by Clara Livingston (friend of Amelia Earhart) and later owned by Laurance Rockefeller. 

What To Do? 

It has been said that Old San Juan has more museums per square foot than anywhere on Earth.  The city itself is often considered a life-size museum of colonial architecture due to the number of buildings that have been declared National Historic Sites.  At the San Juan Museum of Art and History, once a marketplace in 1855, visitors will find exhibits of traditional Puerto Rican art that showcase the island’s rich history. 

Looking for a take-home keepsake? Rum is a critical part of the island’s history – and also a major US export; around 80% of the United States’ rum is made in Puerto Rico. Puerto Rico is the only country that requires its rum to be aged for at least one year, and generally in charred oak barrels, which lends a distinctive, more complex flavor. Skip the Bacardi and go for names like Don Q, Ron Rico, Barrilito, and Ron Llave. 

The island may be known for its 200+ miles of beachfront, but also boasts the U.S. Forest Service’s only tropical rainforest, El Yunque. For a truly unique experience, try a nighttime hike, where you can see bioluminescent mushrooms, insects, and nocturnal creatures. 

Naturally, water activities abound – the best scuba diving is off Cayo Diablo, rare black coral abounds off the island’s southwest coast, and surfers love Rincon – but the most enticing are nighttime swims in the island’s many bioluminescent bays—Mosquito Bay in Vieques and La Parguera in the South are the best known. 

Shop Til You Drop

It’s no real surprise that a U.S. territory would have the best shopping in the Caribbean. Most name-brand stores are in Condado’s Ashford Avenue, where you’ll find names like Cartier, Gucci, and Ferragamo. Should you hit a rainy day, hit up the new Mall of San Juan, which opened this past spring just five minutes from the airport. It features a massive Nordstrom and Saks Fifth Avenue as well as popular shops like Louis Vuitton, Jimmy Choo, and Anthropologie.  

Dine There

Like most Caribbean islands, Puerto Rico’s cuisine – dubbed “cocino criolla” – is a blend of styles, ranging from European to Afro-Caribbean to Latin-American. Enjoy everything from local home cooking at El Jibarito (which translates to “The Hillbilly”) on Calle Del Sol in Old San Juan and a drink at Barrachina, inventor of the Pina Colada (ask for an extra shot of rum) to La Copa Llena at The Black Eagle for an oceanfront setting that serves tapas dishes in a light, bright and tropical decor.

Up-and-coming neighborhood “La Placita” boasts food stalls and markets by day and fun bars and nightlife; hit up Santaella, for local fare from Food & Wine “Best New Chef” winner Jose Enrique. 

As mentioned above, for really special experience, 1919 is the way to go. Diners will experience fresh ingredients sourced from local farmers incorporated onto a menu that changes around 5 times a year to enable this farm-to-table dining. These Puerto Rican dishes are perfect portrayals of the natural bounty of the island - and are always vibrant and enticing. The decor reflects a similar earthy vibe, with muted tones and golden lighting, allowing guests to fully enjoy the experience as they overlook the ocean.

Know Before You Go 

Puerto Rico’s U.S. Territory status makes it one of the few locations one can travel sans passport, making it an easy escape for family and couples alike. San Juan Luis Muñoz Marín International Airport, the island’s main entrance point, is a busy travel hub to many other Caribbean destinations, so expect a line and often long waits through security – be sure to leave extra time. But as a perk, it’s easy to island-hop, or score direct flights to New York via airlines like American, Delta and JetBlue, often $300 or less round trip. If you want to connect to an island like Vieques, a ferry is available, you’re better off with a quick puddle-jumper into VQS instead. 

As of publication time, vaccinated travelers (two weeks after final shots) no longer need to quarantine with proof of vaccination, and all must complete entry-level health paperwork.  

There’s also ample opportunity to tack Puerto Rico onto the front or back of a cruise – as the second largest port in the Western Hemisphere, you can hop on names like Carnival, Celebrity and Royal Caribbean easily, right from San Juan or satellite ports in Ponce and Mayaguez. 

There’s hardly a “bad” time to visit, but high season generally runs through the winter and holiday months, with the best combination of warm temperatures and sunny skies occurring between December and late March. Plan a trip between April and early June for great “shoulder season” deals with little to no chance of hurricanes – but know that May brings the island’s highest chance of rain, usually not much more than an afternoon shower. 

Itineraries

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Mandarin Oriental Canouan Godahl Beach.

Under the radar and up-and-coming Caribbean escapes for those who have been there and done that 

This season, more than any before, people crave rest, relaxation, and a good “week at the beach.” With regulations and rollbacks on openings for many of our favorite European escapes, and concern for some about spending time indoors, beach destinations are consistently among the top choices booked for clients in 2021 and into 2022. 

While we love our regular rotation, we sometimes crave destinations where we won’t see all of our friends and families. 

Most of these island escapes offer direct or easy access, and of course, the peace of mind that comes from fully-stocked resort amenities and services.   

Skip St. Barth’s for … Grenada 

Located south of St. Vincent and the Grenadines and slightly west of Barbados, Grenada and its six smaller sub islands is actually closer to Venezuela than it is to the United States. But thankfully, it’s a direct hop from JFK.

The island offers a number of hotel options, including the boutique chic Spice Island Resort and Calabash Luxury Hotel. But it suffered from a lack of true luxury for years. That is, until Silversands Grenada made its entrance in late 2018. The Leading Hotels of the World property is the brainchild of Egyptian telecom magnate, Naguib Sawiris and design team AW2, which lists resorts like Six Senses Con Dao and Marrakech’s Amanjena on their CV.  

The sleekly modern resort doesn’t sacrifice luxury for charm, offering ample island flair in its 43 suites and 9 beachfront villas, which blend the best of indoor and outdoor living; most rooms offer private terraces and panoramic ocean views. The newness of the property pays off with high-tech touches, like a Tesla Model X house car and a dedicated app for rooms that let guests control everything from temperature and lighting as well as order up extra pillows or in-room dining. Speaking of food, Silversands specializes in locally-sourced cuisine, offering both a fine dining and an Asian-inspired restaurant on property.

Spend your days by the 339-foot infinity pool, the longest in the Caribbean, or on the island’s best beach—Grand Anse—which is conveniently located in front of the property, at the full-service spa, or exploring the island’s rich heritage. Golf is just a few minutes’ drive away.

Grenada, known as the “Spice Island,” has long been famous for its production of (you guessed it) spices, like Nutmeg and Mace. It also boasts cultural attractions in the form of Carriacou, a sister island famous since the 1700s for its sloops, or sailboats, and the Belmont Estate, known for chocolate making, and the unique Molinere Underwater Sculpture Park, the perfect spot to enjoy a snorkel. 

A 48-hour quarantine is currently still in place, even for vaccinated travelers, so this is ideal only for longer stays. 

Getting Here: Grenada is one of the easier off-the-grid escapes, boasting daily direct flights on Jet Blue from JFK, with connections from other East Coast spots. 

Bypass Bermuda’s Pink Sand for … Canouan

Skip the pink sands of Bermuda for another similarly insta-worthy beach, that of the new Mandarin Oriental Canouan, which was briefly known as the Pink Sands Club before it re-opened in 2018 under the Hong Kong based brand’s name. 

Some may know the island, just off the coast of Mustique, part of St. Vincent and the Grenadines and 120 miles from Barbados, as a luxe destination—nicknamed a spot where the “billionaires go to escape the millionaires.” It has a rich history; the resort site formerly boasted a Trump-branded casino and has been managed previously by names like Rosewood and Raffles. But the current project, a 26-room resort made up entirely of one-and two-bedroom suites, plus 13 larger villas, is a complete re-envisioning of the prior iterations. 

Visitors may find the property a bit reminiscent of its Barbadian sister Sandy Lane; the properties share Italian developer Antonio Saladino, as well as a penchant for pink umbrellas. 

Tech-forward rooms are controlled by tablet, a modern touch. Two-room suites are perfect for families with older children or couples sharing a friendly getaway. The resort is small, but offers mighty amenities, including a nine-room spa set into the hillside, and a fitness center complete with Pilates equipment. Enjoy two fine dining restaurants (one international, one Asian), and a Hamptons-style bar, Turtles, as well as a pool lounge offering Peruvian Nikkei fare. 

Spend your days poolside, snorkeling the island’s active coral reef, or on the par-72, Jim Fazio-designed golf course. 

Canouan is tiny, just five square miles, but there’s no shortage of excitement at this tiny spot. Aman is rumored to be in talks about opening a resort on the island. A 120-slip marina at Sandy Lane Yacht Club and Residences was recently opened, and Soho House also has a fairly new location on the island.

The resort still has a short quarantine in place, even for vaccinated travelers. But if you can shelter in place in paradise for a few days (or we can book you an estate with a pool) it’s an ideal escape. 

Getting Here: Hop on the resort’s Citation jet from a nearby island, and perhaps combine with a visit to Mustique, Grenada or St. Lucia? 

Skip August in the Hamptons for … a Family Getaway to Mustique 

Want to know a party trick? Ask someone what Princess Margaret, Tommy Hilfiger, Shania Twain and Mick Jagger have in common. It’s simple – all made Mustique their preferred vacation home destination. Yet another St. Vincent and the Grenadines island, this 2.2-square-mile haven is a billionaire’s playground that lets vacationers play for the cool rental rate of $15,000 and up per week.  

The well-known island has flown under the radar with the misconception that it’s reserved strictly for royalty, billionaires and celebrities, when in fact, it’s a safe and welcoming paradise perfect for families craving a low-key getaway.

The hardest part? Choosing your preferred villa out of the 75 options in the rental pool. Each comes staffed with its own team, complete with housekeepers, chefs and more. We love a few, like the Lavender Hill Cottage, tucked into the hills above L’Anescoy Bay, which is perfect for a couple. The two-bedroom boasts a private yoga studio and beautiful views of the northern part of the island. Hummingbird is a Rockstar option for families, friends, or girlfriend/guys getaways, boasting sleek modern style designed by Italian architect Paolo Piva, 7 king bedrooms, a chef, 3 housekeepers, a gardener and a butler, 2 large swimming pools, 8 acres of private, lush gardens and insane sunset views. Zinnia is our pick for a multi-generational getaway, offering timeless colonial elegance and traditional gingerbread design, four bedrooms, two pools, and a staff of six. 

There’s only one non-villa option on the island, the chic Cotton House Hotel, a former 18th century cotton warehouse turned luxury hotel. It offers 15 suites and cottages plus “the Residence,” its version of the presidential suite. 

The place to gather on the island is Basil’s Bar, which was recently re-designed by the famous Phillipe Stark, but still boasts the same potent rum punches and casual attitude that has drawn guests for decades. 

Days are usually spent by your private pool, in the Cotton House Spa, or taking in one of the island’s more active pursuits. Golf and tennis are popular, as is the island’s equestrian program. Hiking and watersports are also available, and a robust children’s program makes this one of the easier island escapes to go luxe with little ones in tow. 

Getting Here: Mustique has its own fleet of 18-seater Twin Otter aircrafts that run daily from St Lucia, and during high season additional connecting flights are available from Barbados on Friday, Saturday and Sunday. Of course, a private jet isn’t out of the question, either. 

Bequia … Your Boho Island Alternative to the BVIs

Bequia, pronounced beck-way, didn’t have electricity until the 1960s and didn’t even boast formal roads until the 80s… but this boho-luxe island has long drawn low-key travelers that crave an escape from it all.  

Bequia Beach Hotel is one many haven’t heard of, but it’s more than a decade old. Inspired by the neighboring island of Mustique, the resort offers two pools, three restaurants and full- or half-board plans for its 58 rooms, cottages and beachfront suites. Quiet and relaxation are the hallmarks of the island. The clear waters of the Grenadines are ideal for sailing and water sports, and the small but well-appointed spa is an excellent pre-nap activity. 

Newer additions include villas in the Friendship Bay Estate. One of which boasts four-bedrooms, perfect for families thanks to its private pool. There’s also a new 114-foot Italian-built superyacht, Star of the Sea, available for charter for up to 12 overnight and featuring extras like a top-floor Jacuzzi, saloon of rich mahogany, and a lounge stocked with everything from the latest gaming to an extensive film collection.  It’s also available as a day or sunset cruise. 

Getting Here: Take a one-stop flight from New York and other East Coast locals, hop a charter from Barbados, and try out the “we’ll take care of the air” package for week+ stays, which covers the costs of roundtrip flights to and from Barbados or St. Lucia.  

Kamalame Cay … Your Bahamas Alternative 

Just off the Andros Great Barrier Reef in the Bahamas (the world’s third longest barrier reef) sits a 97-acre island best known for its bone fishing, powdery white sand, a serious “shoes optional” policy… and its legendary boozy lunch parties. 

Kamalame Cay is an enforced digital detox (the island boasts barely any Wi-Fi) and a grown-over-time collection of casual beach cottages and suites. Stylish owners David and Michael King-Hew offer up authentic island hospitality in a warm and welcoming environment, and a penchant for inviting friends to visit from all over the world. As a result, boldfaced names keep popping up for visits, like Serena Williams, who spent her honeymoon here, Nicole Kidman, and the late David Rockefeller, for whom the island’s Rock House is named, are among the guest list, although the boldfaced names go on and on. 

It’s easy to spend days exclusively by the beach, fishing, scuba-ing with gear from the on-island dive shop or enjoying a leisurely kayak. Tennis and bikes are also available for those who prefer on-land activity, as well as a chic overwater spa featuring organic OSEA products. Relax in the afternoon with a ‘Samson Special,’ a strong rum cocktail from the island’s bartender of the same name. 

Need something a bit more indulgent? Plan your visit around one of the monthly lunches, a multi-course feast, complete with multi-course meals, DJs, and of course, plenty of free-flowing rosé. Pack your most stylish bikini and tunics – barefoot guests may be, but they trend towards the stylish city dweller and tech-exec types, many of whom fly in or yacht in just for the day.  

Getting Here: It’s a 15-minute helicopter or private seaplane ride from Nassau, or a direct flight on Le Air; charters and ferries are also available from neighboring islands or Miami. 

Itineraries

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Downtown Austin, Texas.

Where to Stay:

Downtown:

Four Seasons channels the coolness of Austin into its typical high-end style - with local art, Texas-inspired spa treatments, to-die-for Margs and Espresso Martinis (as well as Tuna Nachos if you’ve got the nibbles), lawn games, miles of lakeside trails, and view of Lady Bird Lake from the hotel rooms. The Proper Hotel offers an artful immersion into Austin’s culture. There are four unique settings for dining and drink, and a 5th-floor pool deck offering small-batch tequilas and more views of Lady Bird Lake. Hotel Saint Cecilia is a boutique hotel that honors the patron saint of music and poetry and takes inspiration from the era of the late 1960s and early 1970s when rock ‘n roll and beat poetry challenged conventions. Its most renowned feature is the 50-foot heated lap pool which is open 24/7 - and only open to guests of its 14 rooms, just like the rest of the grounds. Commodore Perry feels like a secluded country estate but is really a 10-acre walled oasis in the heart of Austin - very close to the UT football stadium - with cascading gardens and a beautiful courtyard, and typical charming Southern hospitality. South Congress Hotel has a trendy, elegant style, three restaurants, two bars, the locally-famed Mañana coffee shop, a rooftop pool, two boutiques and a motorcycle shop. They like to think of themselves as a microcosm of Austin - and we’d have to agree.

Hill Country: 

Miraval Resort and Spa is perched high among the hills that overlook Lake Travis and puts an Austin-inspired spin on a wellness retreat. You can craft an itinerary around a single intention and stay in a spa-inspired room with breathtaking views, while you attend daily workshops, classes, lectures and wellness activities. Is the yoga barn calling your name? If not, maybe one of the two pools, or the 60+ spa services is. Everything is curated to help you reach your goals. This resort is all about modern aesthetic and has beautiful infinity pools for swimming in. Lake Austin Spa Resort on the other hand is lower in the hills, right on the lake - so, guests can go straight from an Adirondack chair on the dock to jumping into the lake, and is more classic Austin (think wildflowers and Austin Stone). It is rated as the #1 Destination Spa Resort in North America and the #2 Destination Spa Resort in the World by Condé Nast Traveler for a reason. The resort boasts simplicity and serene natural surroundings, the perfect environment to unwind and restore your sense of wellness.

Allen’s Boots on South Congress Avenue

What to See:

Austin is a very outdoorsy city, and classic activities include lots of being outside (making it important to choose a good time of year to go). One of the must-do activities in Austin is Stand-up Paddleboarding on Lady Bird Lake. You can easily rent a paddleboard from Texas Rowing Center and either take a leisurely paddle a little down the lake, or for those more adventurous clients, you can paddle all the way downtown for spectacular views of the city. Zilker Park and Barton Springs are a fun rustic way of getting out and enjoying the weather on a beautiful day. A very lowkey activity, people bring their own snacks, games and picnic blankets and find a spot to plop themselves down and while away the day.

Moving away from active outdoor activities, shopping in South Congress is a must-do. Even for those who aren’t all that into shopping, the murals along South Congress Avenue are iconic. Also, Allen’s is a classic boot and hat store – even if you aren’t interested in buying anything, stepping into the leather smell of the store and seeing the thousands of boots is the icing on the cake of your Austin Experience. For those who are into shopping, there are lots of little souvenir and boutique stores to stop by along the way.

Austin is full of nightlife for clients who wish to partake. The East Side and Rainey are great spots to go and let loose, away from the rowdy college kids. The Parlor and Half Step are fun stops on Rainey Street, and Kitty Cohen’s is a more sophisticated option on the East Side. The White Horse is a classic where clients can go to experience a real honky-tonk vibe. Central Machine Works Brewery is great for music and drinks.

Where to Eat:

Breakfast Tacos and coffee are like a religion in Austin, and we’re here to make sure you get the best. Veracruz Tacos is our top choice for breakfast tacos in the city of Austin (order the Migas, you can thank us later). And, on the coffee front, we’d be hard-pressed to say there’s a better option than Merit - which, lucky for you, there are several locations around the city.

Uchi and Uchiko are sister restaurants that can’t be missed. High-end Asian cuisine reminiscent of Nobu, the menu has something for everyone that loves sushi, fish or Wagyu.

Loro is another must-eat. With long wait times and no reservations, many are tempted to give up on this restaurant. We recommend going on the earlier side, around 5 pm, and your wait time will probably be around 45 minutes. You can grab a drink from the outdoor bar-stand in the waiting area and browse the menu while you wait. Once you are seated it will all be worth it. Each dish is bursting with flavors of Asian-smokehouse-meets-Texas-bbq (a personal favorite is the Oak Smoked Salmon). The drinks are equally as impressive, with the Singapore Sling having a special yuzu-take on the original.

Visitors to Texas have to experience the BBQ, a regional favorite, and the best options include La Barbecue and Franklin’s. La Barbecue has recently moved from a simple BBQ counter to a permanent restaurant location, and offers up some of the best Central Texas BBQ, with the owner creating her own salty and savory rubs that nix the sweet flavors. Franklin’s is a cult-favorite spot that is open for lunch only, and in pre-covid times had an average wait time of 3-4 hours. Today, you can order pick-up and collect it in the parking lot on the same day - giving you more time to enjoy the city while still getting a taste of Franklin’s.

When to Go:

Austin gets hot with a capital H in the summer, so we’d say if you’re looking to enjoy the outdoorsy fun that Austin has to offer, avoid the months of June to October. While we’re at it, we also recommend avoiding May because it’s the rainiest month of the year in Austin. The most beautiful time of year is March/April and November, on the shoulder seasons you’ll miss out on the heat and rain and enjoy the perfect weather for being out in nature and having a great time.

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If Austin sounds like a destination that would suit you, reach out to us to start planning an itinerary curated especially for you.

Written by Michaela Barrett for Lily Pond Luxury.

Itineraries

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The beach at Amanyara.

Find pristine white beaches and barefoot luxury on the Caribbean’s most up-and-coming island. Savvy jetsetters have known about this 40-island chain in the Eastern Caribbean for years, but hotel renovations, buzzy celebrity guests and new direct flights have injected this island with renewed interest for luxury-seeking travelers. 

When to Visit 

With 350 days per year of sunshine, it’s hard to choose a bad time to visit Turks & Caicos. The high season runs from December through April. Temperatures are cooler than many places in the lower Caribbean during peak season—highs hover in the 80s with a light breeze—but as a general rule, the island is a year-round spot. Hurricanes have largely spared the islands; but cautious when booking in the ultra-low season, September and October, as many resorts close or undergo refurbishing projects during that period.  It’s also the highest chance of rain. But in a year like this 

What to Know (Before You Go)

Don’t let the guidebooks fool you. Turks & Caicos isn’t by far the most beautiful of the Caribbean islands – at least on the journey from the airport to your resort. It lacks the pink sands of Bermuda, the mountains of St. Lucia or the captivating culture of Antigua. The 161-square-mile island is mostly flat, dotted with scrub pine and small, single-level homes. 

But don’t let that discourage you. Turks & Caicos is captivating in its austerity, letting its blindingly white beaches and crystal-clear waters do most of the talking. As an added bonus, service is decidedly more “on the ball” than many Caribbean islands, and the locals are among the friendliest we’ve met. Conveniently, the American dollar is the local currency and direct flights are available from most major East Coast destinations. The island is also one of the safest in the Caribbean—parking, and traffic violations are the police’s biggest hassle. 

Stay Here 

Well-heeled travelers have several options depending on their mood. 

Our personal favorite is the barefoot luxury vibe of Parrot Cay by COMO, a 25-minute boat ride from Providenciales. The resort features a villa-style concept, with a series of private pavilions, cottages, and private homes scattered around the island. As much an eco-spa resort as a luxury destination, guests visit for the award-winning COMO Shambhala spa, healthful cuisine, and complete privacy. We’d suggest one of the beach villas, which offer private pools perched on top of a secluded white sand beach, as well as 24/7 butler service.

Many also love the Asian-inspired Amanyara, part of the ultra-luxury chain of Aman hotels and resorts. Located on the 5,000 acre Northwest Point Marine National Park at the far end of the island. The payoff is worth it. Serenity, discreetly attentive service and privacy abound; each room is freestanding and private with views ranging from lagoon and garden to ocean-view villas perched on top of a white sand beach. Highlights include exceptional fitness facilities (think a private boxing studio, Pilates studio, and multiple tennis and pickleball courts) as well as exceptional dining.  

For more accessible luxury (and decidedly more family-friendly locales), choose from a number of high-end resorts right in Providenciales. Our top pick? The centrally-located Grace Bay Club. Opt for sprawling, condo-style residences in three buildings; choose from the family-friendly Villas, the adults-only Hotel and the luxuriously private Estates. Suites offer panoramic oceanfront views and large private terraces with spectacular sunset views. Coming in early 2022, the brand will open a new property – Rock House – which offers a sexy St. Tropez-meets-Caribbean vibe. Individual cottage-style accommodations will feature plunge pools, ocean views, and the resort itself promises fun features like a wine grotto and the longest pool on the island. 

For a bit more streamlined style, we also love the Wymara property, which features spectacular multi-bedroom villas on the other side of the island that offer direct villa-to-water access from private over-water hammocks and docks – one even has a water slide, Maldives style. 

The island also boasts a new Ritz-Carlton resort, complete with signature BLT Steakhouse and a Casino. It’s bound to be a traveler favorite, but truth be told, we prefer the more boutique options for our clients. 

Where to Eat & Drink

Turks & Caicos has one famous dish—conch—and it’s served in varied preparations. Try it raw in ceviche or conch salad, breaded and fried like calamari in cracked conch, or mixed with dough into a hush puppy-like conch fritter. On cool nights, conch chowder also makes an appearance on most menus. 

Get your fill at none other than the aptly-named Da Conch Shack, an open-air restaurant frequented by locals and tourists alike. Go on Wednesday evenings for their famed beach parties and live music or enjoy a lingering lunch any day of the week. 

That said, our favorite option for the local vibe is the unassuming Mr. Grouper. Do yourself a favor and order the signature dish—coconut grouper with mango sauce—served with your choice of two sides. Choose the creamy mac n’ cheese and fried plantains. Not exactly healthy, but utterly delicious.  These local haunts are a short cab from most Grace Bay area resorts. 

Providenciales has its fair share of fine dining, as well, much of which is walkable or a short ($10-$20) cab ride from Grace Bay area hotels. No trip to Provo is complete without at least one visit to Coco Bistro. Make reservations early to dine under the coconut palm fronds at this ultra-romantic restaurant, where tables in high season often book weeks in advance. Savor Caribbean-inspired fare with global influence, like locally-caught tuna sashimi or tandoori-rubbed Mahi with an aromatic chickpea potato cake. If you’re lucky, you might even get a visit from the restaurant’s namesake, Coco the cat. Don’t miss the signature coconut cake for dessert. 

The island’s luxury hotels also offer a number of upscale options. There’s no better place to watch the sunset than from the famous Infiniti Bar at Grace Bay Club. 

Other standout choices for a night on the town include Stelle at the Gansevoort, which serves Mediterranean fare, and Grace’s Cottage, which is located at Grace Bay Club’s sister hotel, Point Grace. 

Where to Play

If you can motivate yourself to get up from your lounge chair, you won’t be disappointed. 

Divers and snorkelers have long known the Turk & Caicos Islands to be some of the world’s best. Calm, crystal clear waters, amazing coral reefs and a wide variety of sea life make diving here fun for any skill level. Wall diving is the preferred pastime; the Turks & Caicos island chain sits atop two limestone banks separated by the “Turks Island Passage” a 6,000-foot channel. If you can, schedule a night dive three to five days after the full moon, when the island’s glowing worms take to the water in a spectacular and somewhat bizarre light show—as the males finish mating, they die in a burst of phosphorescent color that must be seen to be believed. Dive Provo can help you plan an outing.

JoJo the Dolphin.

Leisure seekers should skip the scuba tanks and book a half-day tour with Island Vibes instead. Friendly captains pick you up right from your hotel for a four-hour excursion featuring rum punches, local Turks Head beer and a 45-minute break for snorkeling right along the reefs. Next, you’ll head to Little Water Cay, where you can spot some of the island’s most famous residents, some of the 50,000+ iguanas that populate the Turks & Caicos Islands. While you’re there, the team prepares a fresh conch salad from a just-caught bivalve. It’s the perfect light lunch before you head out again to bask in the sunshine and show off your athletic skills on the boat’s second-story diving board.  You might even spot Jo Jo the Dolphin, the island’s unofficial mascot, a lone dolphin often seen frolicking near tourist destinations.

Want to try something out of the ordinary?  Plan a visit to Potcake Place in the easily-accessible Salt Mills Plaza, an island-based dog rescue that specializes in puppies. Potcake is the name of the wild dogs of the Bahamas and Turks & Caicos Islands. These pups were often fed “potcakes,” or the cake-like mass found at the end of the family’s rice and peas dinner pot.  Show up around 10 AM to the shelter and the friendly team will let you borrow a puppy for a few hours—socializing the dogs and helping them learn basic commands is a key part of the pup’s “re-homing” process. All dogs at the shelter are available for adoption, and most go to U.S.-based homes.  

Of course, relaxation is also on the agenda. There’s no better way to spend the day than lounging in a beach chair, cool beverage in hand, at the hotel spa, or swimming in the crystal clear water.  

Take a stroll from your resort to spend a lazy afternoon browsing the small strip of stores at the Salt Mills Plaza or the Regent Village. Souvenir shops peddle the usual wares, including delicious local Bambarra rum; blend the coconut and dark together with your choice of fruit for a perfectly from-the-islands treat. If you can’t leave without a sparkly bauble, Coco, from the Grace Bay team, is the island’s signature shop offering beachwear from names like Camilla and 9Seed.

Your biggest problem? Once you’ve settled into the Turks & Caicos lifestyle, you may never want to leave.  

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All of the hotels mentioned above offer preferred amenities for Lily Pond Luxury® guests, ranging from complimentary daily breakfast to priority upgrades, hotel credits, and more. Contact your advisor directly to be paired with the perfect property and to plan your trip! 

Itineraries

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Laid Back Luxury Awaits 

The 35-square mile British West Indies island of Anguilla, which is about half the size of Brooklyn, promises some of the Caribbean’s best beaches, food and hotels, all with a covetable ‘barefoot luxury’ vibe. It’s an under-the-radar favorite in a year when travelers are more eager than ever to travel, safely. 

Once upon a time, it was easy to overlook the sleepy island of Anguilla for its buzzier Caribbean counterparts. After all, it wasn’t as close as the Bahamas for a weekend getaway, didn’t have the celeb cachet of St. Barths, and lacked the posh hotels of islands like St. John or Antigua. 

But not anymore. Thanks to daily flights into the nearby island of St. Maarten (an easy ferry ride away) or simple one-hops direct to the island from San Juan, buzzy new hotel renovations, and more than 100 delectable restaurants, travelers are finally discovering just why this tiny island is exactly where they want to be in 2021 and beyond. 

Stay Here

A room at the Four Seasons Resort and Residences Anguilla.

Anguilla’s hotels offer something for everyone, but all of the island’s luxury hotels have something in common. They’re perfect for the barefoot luxury seeker, someone who wants an island escape that feels upscale, but not at all pretentious.

The five-star standard for families and couples alike, Four Seasons Resort and Residences Anguilla, is a striking bluff-meets-beachfront resort and offers everything a lover of the Four Seasons brand would expect, like three oversized pools to Kelly Wearstler-designed rooms and suites with private plunge pools and contemporary neutral décor. 

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Lily Pond Client Perks at the Four Seasons Resort:

• Breakfast for two guests daily*
• $100 resort credit for rooms, $200 resort credit for suites, once per stay
• Early check-in and late check-out, as available
• Upgrade upon arrival, as available

The resort is offering a 5th night free package for 2021, and a 6th night free package for early 2022 visits, combinable with our perks for you!**

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Although the property is nearly a decade old, more than 45 miles of silver travertine marble, high ceilings, and striking natural wood accents make it seem as if it could have been designed in 2021. Unwind in your choice of 181 oversized accommodations, more than 80% of which boast ocean views. 

Cap Juluca Belmond Resort.

For families and groups, we love the spacious four- and five-bedroom villas, each with a private pool, or the oversized multi-bedroom suites, many of which boast full kitchens. There’s little not to love about this newly re-flagged property, which saw a full update of its dining facilities as part of the re-brand. Our new favorites include the aptly-named Sunset Lounge (get trendy with a floral-adorned Frosé cocktail), the waterfront Coba restaurant, and the laid-back Half Shell Beach Bar. Work off the calories in the gym, movement studio, or private spin room designed by celeb-favorite trainer Harley Pasternak. 

The best beach award goes to none other than stalwart Cap Juluca, a Belmond Resort, which is perched on a perfect half-moon swatch of Maundays Bay. The 62-room resort boasts some of the island’s best “on beach” accommodations; many rooms and suites allow guests to step right out onto the sand. The resort also features its own 32-foot boat, perfect for exploring the island. Newly renovated in a Moroccan-meets-Mediterranean-meets-beachy vibe, the property is more intimate than Four Seasons and offers that kind of barefoot in-the-sand luxury that many travelers crave, but is just about 5 minutes away, so it’s easy to visit both properties for dinner. 

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Lily Pond Luxury Client Perks at Cap Juluca:

• Breakfast for two guests per room daily
• $90 resort credit for rooms, $200 credit for suites, once per stay
• Early check-in and late check-out, as available
• Upgrade upon arrival, as available
• $500 gift certificate for stays of $5000 or more, for use within six months of arrival at any Belmond resort worldwide

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Malliouhana, an Auberge Resort.

For a more intimate feel, try the 44 room Malliouhana, part of the Auberge Resorts Collection. Decorated in a contemporary palette of mint, mango, saffron, and white, the resort looks out of a Caribbean dreamscape, complete with whimsical touches like the wall of vintage scuba helmets on one of the entry wall, or the mirrored mosaic tile floors in the lobby. Take advantage of a double-cascading infinity-edge swimming pool perched over the cliffs, two beaches, and a fine dining restaurant that seamlessly melds American, Mediterranean and Caribbean flavors.  You also won’t want to miss a cocktail at the indoor-outdoor Sunset Bar, one of the island’s best spots to catch a technicolor sunset. 

Perks for Lily Pond Luxury Clients at Malliouhana:

• Breakfast for two guests per room daily
• $100 one time resort credit
• Upgrade upon arrival, as avaialble
• Early check-in and late check-out, as available

The resort has an assortment of complimentary night promotions available, combinable with our amenities above.

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Other notable hotels we often book for clients include Zemi Beach House, on the other side of the island, which offers great beaches and a quiet vibe, the intimate Relais & Chateaux Quintessence Resort, which, at just 13 rooms, can also be bought out for families and friends or small weddings, and CuisinArt Resort, re-opening in November 2021 as “Aurora Anguilla” after a complete renovation. It’s also the only property on the island to boast a golf course. 

For groups and families, we can’t get enough of the private-home-meets-private resort option of Ani Villas. A ten-suite estate made up of a four-suite North villa and a six-suite South villa, guests can buy out all or part of the estate and enjoy an all-inclusive stay that includes staff, daily massages, water sports, custom activities and so much more. 

Food, Glorious Food

Anguilla gets top marks for its food – the 35-square-mile island boasts more than 100 restaurants, from the fine French-inspired dining at Jacala to live fire cooking at Ember to Italian at Cip’s by Cipriani to small barbecue shacks that serve slow-roasted ribs and chicken to anyone willing to wander by and pull up a seat on a nearby picnic table. 

Cip’s by Cipriani outdoor seating.

The island’s luxury hotels boast predictably upscale cuisine, but we’d also suggest getting out and about among the local fare for a true taste of island life. One of our favorites was Veya, which offers a mishmash of international cuisine. On our last visit, dishes were inspired by flavors ranging from a layered black bean salad that reminded us of Mexico to shrimp “cigars” that were vaguely Moroccan – an unlikely combination, but everything melded seamlessly as we sat outside in the treehouse of a restaurant and enjoyed the sounds of a live singer doing Sinatra covers at the bar below. 

Other favorites include Blanchard’s Beach Shack, Mangos or Pimms in West End Village, all longtime island favorites.  

Not sure what to order? Most restaurants pack an extensive menu of fresh seafood, but we’d suggest at least one meal of Anguillan crayfish, a small spiny crustacean that looks like lobster but tastes much sweeter and tenderer. It’s best served simply grilled with drawn butter, and available on almost every menu. Our favorite version came from the tiny Sandy Island’s grill. 

Just beware – you won’t feel like getting into your bikini after any of these deliciously filling meals.  

Day by Day 

Anguilla boasts 33 beaches, most of which are made of smooth, pristine white sand and crystal-clear waters, so you could easily spend your entire trip exploring your favorite place to get a tan. But, as with any island, we have a few favorites. 

Meads Bay beach.

Meads Bay boasts a beautiful strip of white and clear blue water that looks right out of your favorite Instagram account. Anguilla isn’t known for rowdy nightlife, but the most happening spot in town is also on the beach – Sandy Ground, to be precise. In high season, you’ll spot dozens of ships docked in the area, but even in quieter times it’s easy to hop from bar to bar enjoying live music, rum punch, and a good mix of tourists and locals. Don’t miss Elvis Beach Bar, known as ‘the king’ of Anguilla nightlife. 

If you really want the private island life, take a short boat trip to Sandy Island or Prickly Pear Cays, both of which offer regular transport from Sandy Ground.  These tiny islands just a few hundred yards offshore boast beautiful white sand beaches, beach-bar style restaurants serving fresh grilled seafood and strong island-style drinks. Prickly Pear is better for those who want to snorkel, while Sandy Island offers beautiful covered daybeds and loungers for napping, drinking and eating, and then napping again. 

If you want to spend a day on the water, we’d suggest the aptly-named Funtime rentals, which offers both chartered services to and from St. Maarten as well as private tours on 12-passenger boats perfect for exploring the island or taking the hour-long boat ride over to St. Barths (weekly on Tuesdays in high season). 

Want something a bit more relaxing? Try a spa day at the Four Seasons, where you can enjoy your treatment with the windows open to hear the crashing ocean waves below, or indulge in a yoga class on the spa deck perched right over the waves. 

Four Seasons Anguilla Spa.

You may want to rent a car for your easy exploration of the island – if you can get used to driving on the “wrong” side of the road you’ll find it easier than expensive cabs. Just beware, the biggest traffic jam on this six-stoplight island is usually the many local (and adorable!) goats that often wander into the streets. 

Getting Here 

Anguilla gets an unfair rep as an island that’s hard to access, but the reality is that it’s just a quick flight and boat trip away. The easiest way to visit is to hop a quick ~four-hour flight from most East Coast airports into St. Maarten and then opt for a quick 7-minute plane transfer or a 20-minute boat charter onto the island. A boat will run about $450 roundtrip per couple, inclusive of entry and departure taxes, and flights are comparable, or $1100 per family.  

These can easily be arranged by the hotel concierge, or we can set them up as part of your pre-arrival. 

Know Before You Go

The island is warm year-round, but high season runs from mid-December through late spring and slows again through the summer, but the privacy, extremely low COVID rates (and required vaccination for all travelers after July) has made this a popular destination for summer too. 

Most hotels for the month of September through mid-October, which coincides with hurricane season, but no other times of year are considered bad – just some rainier than others.  

COVID Entry Requirements

Americans may travel to Anguilla, so long as they receive pre-travel authorization, along with a few other things. Vaccinated visitors to Anguilla must take a COVID test on arrival, quarantine for 7 days on arrival (and test negative again before they can leave quarantine), and have valid health insurance with COVID-19 coverage. However, starting in July vaccinated travelers will not have to quarantine. Anguilla plans to eliminate all entry requirements by October 1st.

Itineraries

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Table Mountain from Blouberg Beach.

Today’s guide is courtesy of Lily Pond Luxury’s Michaela Barrett, a South African native. We’ve asked Michaela to highlight a few of her favorite sites and spots to format an epic South African luxury adventure fit for first-timers and luxury lovers alike!

When to travel (and for how long):

This is a tricky question! Typically, the best time of year for safaris is May to September (the winter) as it is the dry season and will allow the best animal viewing because they congregate around watering holes. However, if you want to experience the beaches and nature in Cape Town more than you want to see animals in a Game Reserve, then November to March will suit your needs better. The recommended length of time to stay would be about 5 days in Cape Town and 3-4 days on Safari, longer if you wish to tack on the Winelands at the start or end.

Where to stay:

All of the luxury properties suggested below offer extra amenities for Lily Pond Luxury clients, including breakfast, credits, and upgrades where available. Ask your advisor how best to select the perfect property for you!

Silo Hotel: This hotel is fairly new to Cape Town’s hotel scene and has quickly risen to the top of the list of luxury hotels in the city. There are only 28 rooms in the modern eclectic hotel, and each room has a private balcony and its own collection of Contemporary African Art. There is also a spectacular one-bedroom penthouse included in the 28 rooms and private residences along the Atlantic Seaboard. There are a few dining experiences available within the hotel that offer incredible views of Table Mountain. The Silo Spa is a great place to unwind.

The Vineyard: This Claremont based hotel has become one of the most environmentally friendly hotels in Cape Town over the past two centuries since the original house was built in February 1800. The architecture is still true to its original English style, but the contemporary interior styling of the house creates a comfortable environment for today’s guests. Hotel amenities include a spa, fitness center, jogging route, and a resident of the hotel since the 1980s that guests will look forward to meeting are the Mountain Tortoises that roam the property. The Constantia Winelands are a short distance from the hotel, and the Kirstenbosch Botanical Gardens are a 25-minute walk, or a 10-minute drive, away.

One&Only: Also located at the V&A Waterfront, the One&Only is also very well located for exploring the city. The rooms are spacious, and guests will have spectacular views of Table Mountain, the Marina, or both from private balconies. The One Above Penthouse offers the ultimate luxurious accommodation experience, with 4 king-sized beds, 2 private pools, a glass wine cellar, and outdoor spaces on both floors. The Nobu restaurant is located in the hotel, along with Isola – a more laid-back restaurant, a bar and lounge, a wine studio, and private dining options. Unwind after a day of sightseeing at the exclusive Spa Island and infinity pool.

Singita Lodges: Singita is dedicated to environmentally conscious hospitality, sustainable conservation, and empowering local communities. Singita means “Place of Miracles” in Shangaan, and that is exactly what this exclusive chain offers. Game viewing is consistently spectacular, as the limited number of guests means fewer people to chase away and interfere with the wild animals. The chain includes 15 lodges across four countries, five of which are in South Africa. Our advisors can help you decide which lodge is the best fit for you, or you could try out a few. Each lodge differs a little from the others, but at the heart of it all is a desire to connect with nature and witness wild animals in their natural state like never. A safari brings out the child-like wonder at the world that everyone should experience at least once in their adult life.

Food in Cape Town

Cape Town is a foodie’s paradise. With the South African currency (the rand) as weak as it is, tourists can enjoy fine dining for a fraction of what it would in the US or Europe. Cult-favorite Nobu has a location in the One&Only hotel and dishes range from $7 to $35 on average (yes, please). Many other restaurants inspired by traditional South African flavors offer the same luxury dining experience – with tasting menus featured at most high-end restaurants – with their own unique atmosphere that sets them apart as their own experience. Fyn is another must-try for foodies staying in the city. With an open-plan kitchen, chic Asian-inspired décor, and an uninterrupted view of Table Mountain and the city below, guests can rest assured they will have a dining experience to remember (and unforgettable cocktails). South Africa is well-known for its wines, and Stellenbosch and surrounds – the Capetonian Winelands – are dotted with wine estates, many of which feature their own special fine dining experiences. Wine Pairing menus and wine tasting are experiences that no wine-lover should miss when visiting South Africa. Some of the Wineland classic restaurants include Delaire Graff, Die Werf, La Colombe, and Babylonstoren.

Activities in Cape Town:

Classic must-sees in Cape Town often include the restaurants and wine estates mentioned above, but there are many more experiences that visitors wouldn’t want to miss. The iconic Table Mountain and Robben Island (where Nelson Mandela and other political prisoners of the Apartheid Regime were imprisoned) are both UNESCO World Heritage Sites and highly recommended for visitors to South Africa to see. The nearby V&A Waterfront is a shopping mall with outdoor entertainment that includes traditional music, and within walking distance is the Zeitz MOCAA (Museum of Contemporary Art Africa) – two fun activities that could be combined into one day. If you’re there in the summer, Kirstenbosch Botanical Gardens and Clifton, Camps Bay and Boulder’s Beaches are beautiful destinations each of which you could easily spend an entire day at. The Old Biscuit Mill in Woodstock is a fun, trendy destination that features boutique stores, food markets, and one of the most highly acclaimed restaurants in the country- ranked in the Top 50 in the World, The Test Kitchen (which you need to reserve at least a month in advance). The Bo-Kaap is a formerly segregated area that is the historical center of Cape Malay culture in Cape Town and the oldest surviving residential neighborhood in Cape Town. It is recognizable for its widely photographed brightly colored homes. Visit the Southernmost tip of Africa at Cape Agulhas.

Your Lily Pond Luxury travel advisor can arrange guided tours to any of these sites at your leisure.

Visas and Safety:

American passport holders do not need visas to visit South Africa for 90 days or less for tourism. Passports must be valid for 30 or more days after the intended return date from South Africa. South Africa is a safe place, but poverty is rife. Keep your belongings close to you at all times, try to use bags that have zippers instead of bags that do not close, and stay in more touristy areas. Be aware of your surroundings and don’t flaunt your wealth and you will be fine.

Stay up to date with the latest COVID requirements using the tools found in our blog about getting back to travel.

Getting there:

You’re in luck. South Africa is one of the easiest places to get to in Africa from the United States. United flies to Johannesburg’s OR Tambo Airport direct from Newark as well as DC (17.5 hours) and then it is approximately a two-hour flight to Cape Town. Generally speaking, travelers will want to spend at least 3-4 nights in Cape Town, possibly venturing into the Winelands, and cap off their trip with a safari.

Getting between safari lodges, with or without COVID restrictions, can require lots of flying. If you’re willing to charter lots of small planes and sit on flights, it’s doable, but if you’re trying to limit the time spent in the air and maximize budget, it’s best to stay within South Africa. for your safari, rather than attempting to spend too much time hopping around. If you chose to do a safari (a highly recommended experience) you will charter a light aircraft from OR Tambo airport directly to your lodge – we recommend the Kruger National Park, or the adjacent Sabi Sands Game Reserve. Both offer prime game viewing and top lodges for a true “safari” experience, without the headache of wasting days in transit.

Venturing to Neighbouring Countries:

The Fish River Lodge.

Neighboring Namibia, Botswana, Zimbabwe, and Mozambique are also beautiful destinations. While Botswana’s safaris are somewhat similar to what you will find in the Kruger, there are a variety of landscapes that differ – such as the Makgadikgadi Salt Pans that you will experience at Jack’s Camp, or the Okavango Delta at Seba Luxury Camp. Namibia is a coastal desert and is home to the breathtaking Fish River Canyon – the second largest canyon in the world after the Grand Canyon. The Fish River Lodge offers an “on-the-edge” experience with incredible views of the canyon below with nothing else as far as the eye can see. Zimbabwe is home to the thundering Victoria Falls and the Victoria Falls Hotel has one of the best vantage points of this Natural Wonder, right across the border in Zambia is the Royal Livingston hotel by Anantara and is incredibly close to the falls, also with an amazing perspective of the “smoke that thunders”. Mozambique is for ocean lovers, and the White Pearle Resort and Azura Quilalea Private Island are two amazing hotels to kick back and enjoy the white sandy beaches. For those on return visits to Africa, trying another country is perfect to expand your horizons. Because once you visit Africa once, you’ll always yearn to return!

Michaela Barrett is a rising Junior at Wake Forest University, where is studying communications and journalism. She is spending the summer with Lily Pond Luxury, expanding her love of experiential travel.

Updated Service Offerings

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If there’s one thing I’m hearing, it’s that you are eager to travel in 2021, or as soon as circumstances permit you to do so safely. 

We’re excited to help you do so in style, and that’s why we are introducing three new types of trips for your planning pleasure. And for those who love our signature services – don’t worry, they’re not going anywhere – you’ll find a brief refresher at the end of what we provide. 

DREAM DESIGNER

The Dream Designer is the perfect experience for the couple, family, or even solo traveler looking to plan for their “travel health” in 2021 and beyond. Much like planning for retirement, travel is something that many of our clients build into their annual budgets.

While experiences like safaris, villa rentals and major sporting event tickets can certainly be arranged at your convenience thanks to our connections, for best rates and space, it’s best to plan ahead.

The Dream Designer lets you practice annual, medium or long-range planning to best organize your travel goals, budget, and schedule. Plan for the next year, milestone anniversaries, a family “wish list” or a post-retirement grand tour. It’s your dream – we just help you plan for it.

The ultimate deliverable is a customized calendar (with optional reminders), inspiration list, and targeted content to get you excited and ready to travel.  

PERFECTLY PLANNED

While many clients love the planning process, others prefer a bit more of a surprise element. Whether it’s a partner looking to surprise someone with a great weekend away, a memorable anniversary, or milestone birthday, we’re happy to work “in secret” and deliver you a Perfectly Planned itinerary, packaged as a gift to your intended recipient.

We’ll even help you deliver the news in style, whether it’s a suitcase of curated clothes chosen by one of our stylist partners, or a great inspiration box of goodies to help you get excited for the trip.

Simply provide dates, a budget, and a mood, and we’ll do the rest, be it booking everything and handing you the tickets, or putting together several choices to let you choose your own adventure.  

POINTS, PLEASE

We’ve long had clients inquire about how to best utilize their points, be it for air, hotels, or anything in-between. We’re happy to say that after many years of searching, we’ve found the perfect partner for these needs, and can now offer this for our clients. Simply let us know how many and what type, and we’ll marry it into any of the above or our signature full-service planning experience.

SIGNATURE SERVICE

Most of you have experienced our signature services already, which includes everything from initial consultation to trip design, custom in-app itineraries, and full-service planning for accommodations, air, activities and more. We’ve long offered services ranging from private jet and yacht procurement to special event and attraction ticket purchases and can almost always add valuable extras to your stay, including breakfast, credits, upgrades and more.

Today’s traveler has even greater need for an advisor’s expertise, as we help navigate the changing world of insurance policies, COVID-19 pre- and post-trip testing, and, in some cases, multi-month trips for our digital nomad travelers. No ask is too big, or too small. 

Itineraries

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MEXICO’S CARIBBEAN COAST SHAKES THINGS UP (NOT JUST COCKTAILS) MAKING THEIR WHITE SANDY BEACHES AN EXQUISITE (and socially distanced) ESCAPE FOR ALL.

Nizuc offers plenty of social distancing spots, plus three beaches.

Just over an hour after clearing customs, we were settled in poolside, sipping tequila and gazing out over calm Caribbean waters and white sands that stretched as far as the eye could see.

It was easy to wonder why people even bother at all with Florida, when the only hassle of this easy escape is packing a passport. The benefits of stunning, oversized rooms with private pools, superior service and true serenity was completely at odds with the area’s reputation for raucous spring breakers.

Riviera Maya, the vast area that starts south of Cancun and stretches all the way down to Tulum, is a hotbed of luxury activity along Mexico’s Caribbean coast.

Just a four-hour flight from NYC, you’ll find a simple weekend away, a no-fuss holiday getaway or a streamlined spring break that lets you do everything you wish... or nothing at all.

HAUTE HOTELS

Much like its Mexican rival, Los Cabos, Riviera Maya boasts its fair share of high- end hotels, each tailored to a unique demo- graphic. Depending on the occasion there are a stunning array of options.

COMPLIMENTARY AMENITIES FOR LPL GUESTS AT Nizuc:

• Upgrade on arrival, subject to availability

• Daily Full breakfast, for two guests per bedroom served in Restaurant

• One-way airport transfer (valid on arrivals only)

• Hydrotherapy session for two, once during stay

• Welcome Amenity in suite: a bottle of tequila and dried fruit

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

For the weekend getaway, choose Nizuc. The 274-room resort offers the amenities of a larger property with the privacy and serenity you’ll usually find reserved for small boutique hotels, thanks to its unique design as a complex of villas and generous rooms (starting from 700 square feet) nestled on 29 acres of protected mangroves. You’d never know it was just 15 minutes from the airport.

Opt for the 2,430-square foot Garden Villa, which offers an oversized private pool, out- door living area and butler service. It’s a worth-it splurge. No matter how short your stay, it’s easy to fill your days or do nothing at all, thanks to six restaurants, two bars, three pools and two beaches, one of which is adults-only. Nizuc also features an ES- PA-branded spa with the best hydrotherapy circuit we’ve tried in years, complete with gratis hand, scalp and arm massage. Use of the facility comes complimentary with treatments of 50 minutes or more.

For dining, Asian-fusion Indochine is one of our favorite restaurants in the area, with a mouth-watering miso-marinated sea bass and seriously good sushi. There’s also fine Mexican at Ramona.

Beautiful multi-bedroom villas at Rosewood Mayakoba are available.

You can’t go wrong with Mayakoba, also just 35 minutes from the airport. It’s a unique 1,600-acre complex of four luxury resorts, a replica Mexican village El Pueblito, and a Greg Norman-designed golf course all connected by a series of man-made lagoons and cenotes. It’s perfect for families, couples and multi-generational groups alike.

COMPLIMENTARY AMENITIES FOR LPL GUESTS AT rosewood, andaz and banyan tree mayakoba:

• Upgrade on arrival, subject to availability

• Daily Full breakfast, for two guests per bedroom

• $100 credit

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

Perhaps the most luxe option is the Rosewood Mayakoba with its impeccable attention to detail and newly-refreshed rooms. However, we slightly prefer the sexy-for- couples-but-welcoming-for-families Banyan Tree Mayakoba, offering an Asian-inspired twist on Mexico. Rooms start at over 2,700 square feet and boast private pools so large that you may consider never leaving your room. Couples will want private living casitas at the Serenity Pool Villas while families will love the two- and three-bedrooms which offer rooftop pools. New villas will be completed in 2020 to add beachfront one- bedroom options as well. Don’t miss Banyan Tree’s Saffron, a delicious Thai standout that draws guests from as much as a 30-minute radius of the resort. Get the yellow curry; you won’t regret it. Rosewood also offers a well-attended beach barbecue on Thursdays that’s also worth the reservation. We love the street food fare at Aqui Me Quedo, which translates to “here I stay,” an apt name for the adults-only poolside spot at Rosewood where we easily spent a few afternoons noshing on tacos and spicy mezcal margaritas.

Another standout experience at Rosewood are regular Ceiba dinners, held weekly in slower seasons and more regularly when the hotel is full. Hosted by the resort’s managing director, guests are invited to gather, family- style, under the resort’s large Ceiba tree in the garden for a communal dinner of fresh and local fare. Limited to about 30 per night and attended by select resort staff as well as guests, it’s a great way to mingle a bit with other travelers in a relaxed atmosphere.

Hotel Esencia’s white sand beach.

Both resorts offer perks like gratis bikes for guests – conveniently labeled with your room number and left outside your door – and stellar five-star spas. The Banyan Tree’s Rainforest Indulgence is a must-try. The 150-minute experience is true decadence, starting with a completely private journey through the spa’s expansive rain showers, saunas and steam room with an eight-step process that involves everything from mud applications to ice baths and hair masks, before ending with a body scrub, Vichy shower and relaxing massage in one of 16 private spa bungalows. Therapists for the spa come from the resort’s other properties in Thailand and Bali, offering an exceptionally authentic taste of Banyan Tree’s Asian heritage.

Families may also want to consider the Fairmont and Andaz properties onsite, which offer top-notch stays at a slightly more forgiving price point. For lunch, we loved

Sotavento at Andaz, an easy beachfront spot that offers a break from Mexican with fresh, simple Mediterranean fare.

Don’t miss the complimentary boat tours, dubbed the Mayakoba Connection. They leave regularly from each resort’s main lobby and connect guests between resorts, as well as impress you with the wildlife and natural surroundings of the complex. You’ll learn from knowledgeable guides about the more than 100 species of birds, dozens of animals and more than a dozen crocodiles that live on property, as well as get a sneak peek of the more than 20 onsite dining options. If you want to visit El Pueblito, the village with shops and snack spots, play a round of tennis, or learn to make ceviche at the cooking school, you can also ask for a golf cart or evening SUV shuttle between resorts; the boats only run during daylight hours. There’s also a small chapel perfect for weddings or vow renewals.

COMPLIMENTARY AMENITIES FOR LPL GUESTS AT Belmond maroma, hotel escencia, chable maroma and viceroy riviera maya:

• Upgrade on arrival, subject to availability

• Daily Full breakfast, for two guests per bedroom

• $100 credit

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

There are a few other standouts in the area. For those who wish for a true “old Mexico” feel, opt for the private Hotel Esencia, an intimate escape that was once the private home of an Italian Duchess. Esencia also features a Michelin-starred chef formerly of Spain’s famed El Bulli. At a more accessible price, there’s Viceroy Riviera Maya, where each of the 41 rooms is an individual casita with private plunge pool. For a beachfront get- away, the Belmond Maroma is located on the best beach in the area and offers many rooms with gorgeous ocean views – a rarity along this stretch of Mexican coast as so many hotels specialize in lagoon or jungle view. Both Viceroy and Belmond regularly offer dining plans to make them more cost- inclusive.

Rooms at Viceroy Riviera Maya

We love all three of these properties. Esencia can easily be the most expensive in the area, but it’s quite remote, so it’s best for a couple’s escape where you don’t wish to leave the resort. Both Viceroy and Belmond offer a more “authentic Mexican” vibe, while still blending high-touch service and exceptional dining and spa offerings as well.

Speaking of all-inclusive, if you’ re traveling with a large family or friends, Grand Velas is an excellent option.

For a girlfriend getaway or wellness escape, we’d opt for the new Chablé Maroma, opened this spring. It’s the second property from the brand – the first is inland near Merida. Think of it as wellness lite; you can still enjoy plenty of tequila but also try a temazcal (a Mexican sweat lodge) or meditate under an

Alamo tree, a plant considered sacred to the Maya. Or, keep it simple with a familiar deep tissue massage and private yoga class. To get truly in touch with your inner hippie, head onward to Tulum, about 90 minutes from the Cancun airport, where options like Nomade or Be Tulum are as Insta-worthy as they are luxe. While here, try creative smoothie bowls at Matcha Mama, mezcal cocktails at Gitano (yes, the same one that’s in NYC) and farm-to-table fare at El Zorro Plateado.

SARGASSUM – IT (LITERALLY) STINKS

We’ d suggest checking the sargassum situation before booking. The unattractive and malodorous seaweed has been plaguing the Mexican and Caribbean coasts for years now. But don’t pass on the destination entirely. Resorts are doing their best to keep up but watching for live cams, checking with your travel advisor or calling the resort directly can keep you from disappointment. The sea- weed comes and goes, so you may see some one day and virtually none the next.

WORTH LEAVING THE RESORT

Truthfully, Riviera Maya makes for an easy fly n’ flop destination – and sometimes, that’s exactly what we need. For a long weekend, we’d suggest picking a complex with a few options for activities, like Mayakoba. New this season is a 55’ Van Dutch charter yacht, perfect for a full- or half-day trip out to Cozumel or a sightseeing tour for those who simply want to get off campus.

But if you wish to get out into the local culture, plan a day or half-day to sightsee with a driver/guide; every resort can arrange boat days or tours to major sites. If you’re visiting for a week or longer, resort hopping can also offer a nice change of scenery. We’d suggest mixing something like the new Chablé Maroma, which is geared toward wellness, with something a bit more foodie, like Nizuc, or pairing the remote Hotel Esencia with Rose- wood Mayakoba or Belmond Maroma.

Other attractions worth trying are Chicen Itza, the 1,200-year-old complex of pyramid- like Mayan Ruins, a UNESCO world heritage site and one of the new Seven Wonders of the World; try to go early to avoid the worst of the crowds. Prepare for a long day as it’s about a two-hour trip each way. Lesser ruins, like the Coba near Tulum, are slightly closer.

Another option is an early morning dip in one of the many local cenotes, natural underground water sources that create crystal clear pools teeming with wildlife.

We’d pass on the big clubs in Cancun – pretty much anything in the hotel district feels tourist – or venturing beyond the main drag of 5th Avenue in Playa Del Carmen. After all, who needs shopping or nightlife when white sand and clear water await?

WHEN TO VISIT

Riviera Maya is warm and sunny year-round, although, like any Caribbean climate, it’s prone to an occasional rainstorm. There’s no “bad” time to visit, but we usually skip travel from late June through October, when the chance of hurricanes is the highest, and the humidity and bugs put a damper on the fun.

THE PACKING LIST

Flowy caftans by Camilla, a stunning suit by Norma Kamali and a Eugenia Kim sun hat fit in nicely; for men, shorts + Swims by day and linen slacks and a button up (no need for a jacket) by night work just fine.

GETTING HERE

Daily nonstops are available from most destinations on the East Coast, with regular offerings from the West Coast and Midwest.

SAFETY FIRST

We often hear rumblings about safety concerns in Mexico. It’s a personal choice, of course, where you wish to travel, but we turned to the experts at Andrew Harper’s Hideaway Report for a little extra insight:

Although travel alerts have been issued recently for the Mexican state of Quintana Roo, and specifically the resort city of Playa del Carmen, there is little immediate cause for alarm. There are no restrictions placed on U.S. government employees in the region, and travelers are urged only to “Exercise Increased Caution.” The incidents that have attracted attention have primarily been a result of turf war- fare between rival gangs.

In a post-COVID world, safety is a matter of both healthcare and preference, but we find Riviera Maya to be ideal given the large room spaces, ample outdoor dining, and sprawling resorts that make it easy to socially distance.

This story originally appeared and has since been updated from the Fall 2019 issue of Woodbury Magazine, where McLean writes quarterly travel journals.

Itineraries

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Edinburgh Explorations

Upon arrival to Edinburgh (the easiest gateway from the U.S.), head directly for the top choice in the city— Balmoral, a Rocco Forte Hotel. Perfectly positioned on Prince’s Street, just moments from Waverly Station, the Victorian-era hotel evokes a castle—complete with turrets and moody stone. The iconic clocktower dome that’s visible from both the Old City and the New is a bonus way to find your bearings as you explore.  We’d suggest at least two nights, but if you wish to sightsee at a leisurely pace, three is ideal.

Complimentary Amenities for LpL Guests at The Balmoral:

• Upgrade on arrival, subject to availability

• Full Scottish breakfast daily for two guests per bedroom served in the restaurant

• $100 USD equivalent Food & Beverage credit to be utilized during stay (not combinable, no cash value if not redeemed in full)

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

A mix of classic and contemporary, the recently-renovated rooms boast a chicly-natural palette of greys and soft pastels by Olga Polizzi (sis to Sir Rocco, for whom the brand is named), with pops of green, brown and grey, meant to evoke the Scottish landscape, plus cheeky modern photos featuring Sean Connery as James Bond, and touches like luxe marble baths with heated towel bars and Asprey amenities.

Ask for a peek behind the purple door and owl-shaped knocker into the J.K. Rowling Suite, so named because the author finished Harry Potter and the Deathly Hallows in the hotel. There's even a bust of Hermes signed by Rowling herself in the room. 

View from Camera Obscura on my tour with Ian Black.

Don’t linger too long—although it’s tempting, either over afternoon tea in the Palm Court or in the well-appointed spa, the largest in the city—as there’s much to explore. While a guide is certainly a great way to see the historic sites, we loved a slightly different take. Book top photographer and Insta influencer Ian Black for a two-hour photo safari (from GPB 150 for a half-day), and hit everything from aforementioned Calton Hill (a UNESCO World Heritage Site that boasts everything from Parliament to the unfinished National Monument, plus great views) to a stroll up the Royal Mile, an aptly named stretch of the Old City that stretches between the two royal residences, Edinburgh Castle and the Palace of Holyroodhouse. While pointing out the best vistas (Camera Obscura, the highest point in the city and the town’s oldest tourist attraction) to historic facts (like a peek inside the Thistle Chapel, where the Queen bestows Scotland’s highest honor at St. Giles Cathedral) we found ourselves stopping for photographs along the rainbow-colored Victoria Street, pausing at various alleyways and walkways (known to the Scottish as “closes”) and ending at The Vennel, where you’ll be just below the famed Castle.

By afternoon, pick your poison – we’d opt for lunch at a spot near the hotel like Café Royal, a great spot for local oysters and seafood that’s been in business since 1826, before heading out to the Palace of Holyroodhouse, a working palace still houses the Queen and other members of the Royal Family during the annual “Royal Week” in Scotland each summer.  The self-guided audio tour takes 60 to 90 minutes, mixing everything from the majestic (yes, the Queen still receives in these rooms) to the macabre (bloodstains from a 16th-century murder). Then, head to Edinburgh Castle, which once served as the city’s primary fortress, as well as a royal residence until 1633. Today, it’s best utilized during the annual Edinburgh Military Tattoo, which takes place each August during the city’s robust festival period.

A view of the Balmoral Hotel from Princes Street.

Should you wish to take a break from the history books, Princes Street, where the hotel is located, offers a wealth of options for shopping, but we’d bypass the expected tourist destinations peddling tartan scarves and mass-market shortbread for a pop-into nearby Hamilton & Inches, a top jeweler in Edinburgh and the only place in the world where Scottish gold jewelry is available, as well as intricate silverworks made locally by a father and son team. For something a bit less precious, hit up Strathberry, beloved by the Duchess of Sussex, amongst others. Their bags feature Spanish leather, but all of these understated accessories are manufactured right in Edinburgh. For a bit of tweed to take your Scots style up a notch, hit Walker Slater (there are two, one for men and one for women) in the Old City, where you can outfit for a made-to-measure look or purchase off-the-rack.

Complimentary for LpL Guests at The Fife Arms:

• Upgrade on arrival, subject to availability

• Daily Full Scottish Breakfast for two guests per bedroom

• $100 USD equivalent Food & Beverage credit to be utilized during stay (not combinable, no cash value if not redeemed in full)

• Dean's Angus McCoo Shortbread

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

But for a real taste of Scottish handicraft, we’d ask the Balmoral to arrange a private session down in Leith (a trendy waterside neighborhood) with Araminta Campbell. The 30-year-old boasts her own studio with two 19th century looms, making alpaca and cashmere-based textiles ranging from luxe blanket wraps to custom-designed tartans and bedding. You can see the process at work or create a tweed or tartan for yourself (from 1500 GBP for the design session).  Like what you see? If you head to the Highlands, you’ll catch her fabrics at the over-the-top Victorian coaching inn turned haute hotel The Fife Arms in Braemar, home of the famous Highland Games, an annual test of strength and stamina attended by the royal family. 

While down in Leith, plan a quick tour of the Royal Yacht Britannia, which served as Queen Elizabeth’s royal yacht from 1954 to 1997 and hosted everyone from Nelson Mandela to Ronald Reagan.

A suite at the Fife Arms in Braemar.

Whiskey lovers will also want to pause for a dram at the Malt Whiskey Society. While it’s technically a private member’s club, the Vaults at Leith offers private tastings of limited-edition single malts – many of which can’t be found elsewhere. Find a flavor profile you love? Head back to Balmoral’s hotel bar, Scotch, for a sampling of 500+ rare and top-notch whiskeys to further refine your palate.

For dinner, don’t miss tried but true The Witchery by the Castle, which earns its name from the hundreds of “witches” burned at the stake in the 16th and 17th centuries on nearby Castlehill.  Today, it’s a romantic, candlelit fine dining experience located in a historic Old City close. For a post-dinner nightcap or more casual yet still elevated pub fare, stop by The Devil’s Advocate, a dimly lit cocktail bar in an old Victorian pump house.

Other options for a top-notch stay include The Caledonian, a Waldorf-Astoria hotel with great views of the Edinburgh Castle from more rooms than any other hotel in the city. For boutique options, we love The Scotsman, located in the original home of the newspaper bearing the same name, as well as Fingal, a luxury yacht turned 23 room floating hotel in Leith.  

As lovely as Edinburgh is, don’t make the mistake of thinking that you’re done. You can certainly pair with another city – Glasgow makes an easy secondary addition – but we’d recommend heading a bit further afield and exploring.

Pair another three to four nights with your chosen activities, including:

The Greatest Game

Invented in Scotland and documented as far back as the Middle Ages, and today, the country boasts more golf courses per population head than anywhere else in the world.  

Complimentary for LpL Guests at Gleneagles:

• Upgrade on arrival, subject to availability

• Full buffet Breakfast

• $100 USD equivalent Food & Beverage credit to be utilized during stay (not available in Restaurant Andrew Fairlie or in-room minibar, not combinable, no cash value if not redeemed in full)

• Early check-in/late check-out, subject to availability

• Complimentary Wi-Fi

While the Old Course at St. Andrews, which dates to 1574, is by far the country’s most famous, there’s great golf to be had almost anywhere you wish to go. For luxury that even a non-golfer can get behind, don’t miss a stay at Gleneagles, about an hour each from Glasgow and Edinburgh by car. The grand resort (which hosted the 2014 Ryder Cup and boasts four unique courses) dates to 1924 and still has a Roaring Twenties meets Scotland vibe. Dubbed “Riviera in the Highlands,” it’s a meticulously renovated grand resort in the very best sense of the word. 

Perfect for couples or the whole family, let the team of “playground planner” concierges fit you in Hunter boots and Barbour jackets to take part in an array of outdoor pursuits from clay shooting and fly fishing to off-roading in a custom-outfitted fleet of Land Rovers before unwinding in the ESPA-branded spa or indulging in a perfect gin martini prepped via table-side trolley at The American Bar. After all that activity, you’ll want to recap the day over a candlelit dinner at The Strathearn restaurant, where you’ll indulge in a tasting flight of smoked salmon or a theatrical table-side flambé of filet mignon, retiring sated and full to newly-renovated rooms done in thoughtfully muted earth tones with pops of brass, leather, and tweed. Book one of the Estate Rooms for the best views over the scenic Ochil Hills and grounds. It’s easy to fill your days with activities on the property, linger leisurely over afternoon tea (yes, they have an entire restaurant dedicated to it) or use the hotel as a home base for further explorations.

The American Bar at Gleneagles

Whiskey Wanderings

There’s no shortage of whiskey in Scotland with more than 120 active distilleries producing across five major regions. For a connoisseur, the country can’t be beaten. But for the rest of us, if you’ve seen one or two distilleries, you’ve seen them all. If you can head up north, one to make time to see is the newish Macallan distillery, in the heart of the country’s Speyside region. It took six years and more than $186 million to build, and today boasts 36 copper stills as well as nearly 1000 bottles of The Macallan dating back as far as 1936. Pair the visit with a base in Inverness (we love the newish Ness Walk hotel) and a bit of sightseeing like the famed Culloden Battlefield and of course, a trip to see if you can catch Nessie along the Loch Ness, the largest lake in the UK.

Can’t stand the smoky stuff? Not a problem. Gin is the country’s second-most-loved drink, with many local varieties offered in the form of spritzes, martinis and tonics, and local vodka (we loved Ogilvy) is also a treat. Gin elevates everything, from tea to happy hour, as does elderflower, another local herb often used in liqueurs.

Dining at Glenapp Castle

Highland Highlights

From the magnificent Ben Nevis, the country’s highest peak, to Cairngorms National Park, which offers some of the world’s best dark sky stargazing, to the iconic “Harry Potter” Jacobite Steam Train along the country’s western coast, it’s hard to head to Scotland feel like you’ve really seen it if you skip the Highlands.

Don’t miss a few days in the countryside, blending luxury hospitality at a spot like Inverlochy Castle, The Fife Arms or Cameron House (re-opening later this year) and take a few days time to see the country’s many castles, ruins, parks and more.

Speaking of castles, it’s hard to drive what feels like more than a mile without seeing a ruin or historic marker sign. While it’s tempting to pause at every spot, make time for a few major sites to avoid castle fatigue. We’d suggest Stirling Castle, about 30 minutes outside of Edinburgh, childhood home of Mary, Queen of Scots and yes, a fixture in movies like Braveheart. While you’re nearby, hit up Linlithgow Palace, her birthplace and a magnificent ruin, as well as Doune Castle, another Outlander filming site that also doubled as the setting for Winterfell in the pilot of Game of Thrones, as well as the famed castle in Monty Python and the Holy Grail.

Culzean Castle made a fun day trip during our visit to Glenapp.

 Today, many castles and noble homes are available for visiting. Glenapp Castle, a Relais & Chateaux gem in the south, is one of our favorites, both for its gorgeous views of Alisa Craig island and for its quiet beauty, with 36 acres of landscaped gardens and activities like falconry and even a glamping program available in warmer weather. While there, plan a day trip to Culzean Castle, a cliff-top masterpiece with a country park, miles of trails, and a home that once housed private apartments of General Eisenhower.

Perfectly Planned:

But, Will it Rain?

Will it rain during your visit to Scotland? Most certainly. The Highlands get measurable rainfall more than 250 days each year, and other areas get rain up to 175. As the locals say, however, if you don’t like the weather, wait a minute and it will likely change. Just pack layers.  

Peak spring break months top out, generally, in the mid or upper 50s, while summer stretches in to the 60s and 70s, with lovely long days, that, towards the north, areas like Orkney, Skye and Loch Ness, may mean as many as four hours more daylight than London. It’s light up until almost midnight in most areas, allowing you to see and explore into and past the early evening in most cities.

August is a particularly good month, crammed with a festival nearly every weekend that infuses the city with a buzzy vibe. The Edinburgh Fringe Festival, a mix of art, music and theater events held at locations around the city, is one of the largest of its kind in the world. Hotels will rise to premium rates at this time, so be sure to book early.

Fall is also lovely—particularly if you fancy catching the heather in bloom across the Highlands or want a leisurely round of golf before a roaring fire and whiskey come the evening. Winter isn’t the optimal time to visit, but it does offer one bright spot— the festive period of Christmas, Hanukkah and New Year’s Eve, known as ‘Hogmanay’ in Scotland, are packed with great three-, four- and five-night activity packages for the whole family at most resorts, ideal for an alternative to skiing or the Caribbean for adventurous families.

Getting There:

Scotland is a relatively inexpensive option for European travel, with tickets often below $600 in Economy from major East Coast gateways.

Getting Around:

Yes, you’ll drive on the “wrong” side of the road in Scotland, but roads are well-marked and in miles, making, for the most part, driving a relatively simple task. Uber works in major cities, but private drivers are an easy fix for avoiding any hassle. Use a reputable tour planner like yours truly and we’ll get you all set up.

A Double or Triple Feature:

While Scotland certainly makes for an easy enough trip by itself, it’s easier than ever to add Scotland to a larger UK trip or a European Grand tour. Make it a 5-hour train from London to Gleneagles, or a quick nonstop from Heathrow into Glasgow, Edinburgh, or even Inverness. From Edinburgh or Glasgow, most major European cities are within a two or three-hour flight at most.

The most logical pairing would be to start or finish with London or Dublin, adding in 4 or so nights to visit London and then pairing with a few nights in major cities or a week or more in Scotland. Ireland is another easy combo; we’d suggest just two nights in Dublin plus any additional driving you wish to do around the country or mixing a week in each destination for a true taste of the UK.

If you’ve visited the major tourist sites previously, Amsterdam is a well-considered addition, particularly it offers a direct flight back to JFK.

One thing is for certain, however. One visit to Scotland and you’ll have the urge, as all road signs point to as you leave a city, to “haste ye back” as soon as possible.

This piece originally appeared in the Spring 2020 issue of Woodbury Magazine, written by yours truly.

Itineraries

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WELCOME TO WINE COUNTRY

To an outsider, Napa is often thought of as a singular destination — a city where wine is plentiful and vineyards stretch as far as the eye can see. It is, technically. But what many don’t understand is that the Napa Valley itself is not just one place, but simultaneously a sprawling and densely-packed area, more than 30 miles long and five miles wide, and part of an even larger 700 square mile Napa County. The area includes over 475 vineyards and more than 1,000 distinct wine brands. Despite all the hype, the Napa region still produces just 4% of the state’s total wine, the majority in small-batch, high-quality production of grapes like Cabernet Sauvignon and Chardonnay, many of which are reserved just for those visiting the vineyard and/or wine club members. Moral of the story: if you’re looking for something special, you’ ll almost certainly want to make the trip in person.

In order to divide the valley into more navigable areas, visitors tend to call Napa by wine-focused sub-sets: the foodie Yountville, the small towns with big wines of Cab-heavy Oakville and Rutherford, posh St. Helena, boho-chic Calistoga, and the up-and-coming Napa proper. To plan the ideal visit, it’s important to plot out not only what you want to drink, but the overall feeling of the visit — is it a tasting menu extravaganza, a wine buying spree, a girls’ weekend of wine and spa, romantic reconnection? Whether it’s your first trip or you’re a seasoned collector, Napa’s diverse mix of hotels, restaurants, and wine-focused experiences offer something for almost everyone.

Calistoga
Romantic getaways + wellness escapes

Many rooms at the Four Seasons Napa Valley overlook the working onsite vineyard, Elusa Winery.

For a leisurely visit of three days or more, begin in Calistoga at the north end of the Valley, where the mountainous scenery instantly puts one in vacation mode.

Complimentary Amenities for LpL Guests:

• Upgrade on arrival, subject to availability

• Full breakfast daily for up to two guests per bedroom

• $100 USD Resort credit to be utilized during stay

• Early check-in/late check-out subject to availability

• Complimentary Wi-Fi

Romance seekers should look to the newly opened Four Seasons Resort & Residences Napa Valley. The hotel is creatively nestled into the middle of a working vineyard, Elusa Winery, allowing for spectacular views throughout the property. Wander the grounds and you’ll find the 85 rooms and suites laying low between olive and oak trees, while the residential villas showcase views of the vineyard. Each room offers ample privacy, and all feature fireplaces and private terraces. It’s also one of the few resorts in the area offering multi-bedroom lodges with full kitchens, perfect for families. It would be easy to check into this resort and never leave – hiking trails, two sparkling pools, and an onsite vineyard are perfect for those seeking a little R&R. Your time in Calistoga (a renowned spa & wellness destination) wouldn’t be complete without a trip to Spa Talisa. Bathe in mineral-rich whirlpools or indulge in their signature mud & sun experience for the ultimate renewing treatment.

Just across the way, the Auberge resort, Solage, embodies a chic vibe with whitewashed buildings and a fresh, youthful spirit. We’d definitely recommend booking for a girls’ weekend or a spa-focused escape here. Their modern signature restaurant, Solbar, is a must-visit, dishing out fresh and flavorful California cuisine in a contemporary setting. The menu is evenly divided into “hearty” and “healthy” categories so you can decide how much you want to indulge.

Calistoga proper is just a ten-minute hop away. While the shopping isn’t grand, it’s still easy to spend an afternoon exploring the city’s small local bookstore, home, and apparel boutiques, or indulging in a signature soak in the area’s many mineral springs or mud baths.

Standout dining spots include Lovina, offer- ing New American fare in a historic Craftsman home. When featured on the menu, definitely order the chef’s play on chicken tikka topped with homemade lentil chips. If you’re in the mood for a tasting, end your stroll downtown at Tank Garage, which makes its home in a chic vintage service station. We also love the Calistoga Wine Stop, located in the town’s old train depot. Owner Tom Pelter specializes in local offerings and has been selling and talking about wine for more than 30 years. Ask him to make you up a case of local favorites, select the best bottles for cellaring, or even help decide the pairings for your next dinner party. We think of him as a one-man wine club without the recurring subscription.

It’s always best to make wine tasting appointments in advance, particularly if you’re looking to hit the big names like Schramsberg, known for its bubbly, or Chateau Montelena, designed to look like an authentic castle. Montelena is a name you likely recognize – it’s the winery known for putting California grapes on the world’s stage in the 1976 famed “Judgement of Paris” wine competition, as well as the setting for the 2008 comedy Bottle Shock. Don’t want to wait in line? In-the- know guests head to Davies Vineyards, the parent company behind Schramsberg, where you can also sip the sparkling stuff out of its St. Helena tasting room, as well as their red offerings under the name J. Davies.

VISITORS TEND TO CALL NAPA BY WINE-FOCUSED SUB-SETS TO DIVIDE THE VALLEY: THE FOODIE YOUNTVILLE, THE SMALL TOWNS WITH BIG WINES OAKVILLE AND RUTHERFORD, POSH ST. HELENA, BOHO-CHIC CALISTOGA, AND THE UP-AND-COMING NAPA PROPER.

However, one of the best ways to experience the area is to enjoy a small producer that offers that only-in-Napa experience. We love Frank Family Vineyards, owned by former Disney president Richard Frank. This vineyard is one of the few in Napa to offer an impressive collection of bubbly, white and red wines, many of which are named after Frank’s beloved dogs. Many days, you’ll even find Frank himself greeting guests.

St. Helena
In the center of it all

Those looking for a more walkable retreat should try St. Helena as their home base. Thoroughly central, St. Helena offers no shortage of places to stay, from the country- club chic Meadowood, with its eponymous 3 Michelin-starred tasting menu hotspot, the Restaurant at Meadowood, to the sleekly modern Alila Napa Valley, a Luxury Collection Hotel, which offers walk-to-town positioning and expansive balconies with firepits overlooking the Beringer Vineyards, the intimate Ink House, or the quietly charming Harvest Inn.

Spa Lounge at Alila Napa Valley.

We find St. Helena to be the truest “town” in the valley. Its popular Main Street is a delight, where you’ll find everything from the 90-year-old Model Bakery, a Napa institution boasting English muffins so delicious they’ll make you rethink giving up carbs, to the quirky Martin Showroom, which, on a recent visit, boasted a $3.9 million T-Rex skeleton named Roosevelt amidst modern sofas and the latest chic coffee table books.

Throw a stone and you’ll hit some of the valley’s best wineries. The new and darkly sexy tasting room for The Prisoner is a must-visit, offering reds and whites at more affordable price points than many in the valley. We’ll return again and again to Hall, which offers excellent Cabernet Sauvignon, as well as more than 33 acres of gardens with an impressive collection of over 35 pieces of sculpture and modern art. Appointments aren’t required, a rarity in Napa, so you’ll also be able to come and go as you please. Actually, some of the best experiences you’ll have here are the ones you won’t even have to book ahead or online. We can help curate custom gastro tours with invite-only wineries and chefs, bike and wine excursions, or visits to by-invitation-only wineries for our clients.

For dinner, pass on at least one tasting menu evening for the rotating selection of gourmet chicken wings or the burger at The Charter Oak from Christopher Kostow of Meadowood fame, or skip the wine for a night and try a craft cocktail from speakeasy-style local favorite Goose & Gander.

Oakville & Rutherford
Where the serious wine drinkers come to play

Just a few minutes down the road, Oakville and Rutherford offer up some of the area’s top vineyards and one standout hotel property. Auberge du Soleil, sister hotel to Solage, dominates with its hilltop restaurant, another Michelin-starred spot, offering one of the most romantic experiences available in the entire valley. For atmosphere without the $1,000-plus-per-night and up price tag, snag an outdoor table for lunch or a late afternoon drink at the no-reservation-required bistro on property.

These towns have no shortage of hard-hitting winery experiences and Cabernet Sauvignons that cost as much as your plane tickets from New York. Interested in the art of winemaking? A must-see is Palmaz Vineyards, one of the most high-tech in the valley, built into an 18-story cavern at the base of Mount George. For bragging rights, book into the newly-open-to-the-public Newton, part of the LVMH portfolio, which name drops Dom Pérignon, Krug, Veuve Clicquot, and Ruinart in their book of booze. To truly inspire jealousy amongst your wine-loving friends, grab a hard-to-get visit to only-available-with-the-right-strings-pulled Harlan or BOND, both of which boast lengthy waiting lists for their wine clubs. Hint: BOND is on this year’s Camp Napa visit list.

Yountville
Foodie focused

The French Laundry is a restaurant that has put — and kept — Napa dining on the map

for decades, and if you’re coming to worship at the altar of Thomas Keller, there’s no better place to do it than in Yountville. This is where he boasts four distinct dining ventures: the prix fixe French Laundry, which books exactly two months in advance; his signature Bouchon Bakery, where we encourage you to get both bread and a homemade Oreo; the decidedly less pricey $58-per-person prix fixe Ad Hoc + Addendum, where we recently tried the best-fried chicken on the planet; or his newest venture, a Mexican/Oaxacan spot called La Calenda.

There’s no better place to stay than the sleek Bardessono, built from salvaged stone and reclaimed wood, boasting LEED Platinum certification. It feels modern without veering at all into crunchy California territory. While you’re there, wander across the street to RH Yountville, a Restoration Hardware concept store offering a sleek restaurant perfect for brunch or lunch. Finish with an elevated tasting experience in Ma(i)sonry, a two-story wine vault in a more than century-old stone home. Youʼll experience unique flights from hand-selected area producers, many of which donʼt offer tasting experiences elsewhere. Weather permitting, lounge on comfortable sofas and enjoy your drinks in the trellised outdoor garden surrounded by olive trees and chandeliers.

Let’s be honest, we never thought we’d be so excited to visit an RH either, but their restaurant was a highlight brunch of a recent visit. Be sure to stay for a wine flight.

Napa
Buzzy + youthful

For years, downtown Napa offered little more than a stop on the way to “real” wine country, but recently, itʼs become a see-and-be-seen destination unto itself, full of new boutique (and well-priced) hotels like the Andaz by Hyatt as well as the Archer, which boasts the cityʼs only rooftop bar (Sky & Vine) as well as a Charlie Palmer Steak restaurant. Wineries like the new Ashes + Diamonds offer stylish midcentury modern décor, and in Napa proper, youʼll find actual nightlife beyond 10 pm.

Pop in and out of tasting rooms and shops as well as spots like Bounty Hunter, a popular wine shop, barbecue restaurant and tasting room that offers a standout selection of more than 400 top bottles. We could easily spend a day here in Napa _ starting with a cooking class at the Culinary Institute of Americaʼs (CIA) at Copia campus, browsing local shops at First Street Napa like the collection of artisan makers at Makerʼs Market and the food-focused Napastäk Napa Valley _ or the Oxbow Public Market, a unique collection of food stalls and farm-to-table vendors offering everything from oysters to fresh-pressed juices and one of the areaʼs only distillers.

New on the scene and just 10 minutes from downtown, Stanly Ranch, an Auberge Resort, is sure to steal your heart. Impeccably designed and surrounded by 700 acres of historic working ranch land, the Stanly will offer 78 guest rooms & stand-alone cottages. Each accommodation is meant to feel like a home away from home, with its warm neutrals, outdoor firepits, and open seating areas– perfect for sipping a glass of Napa wine. If you’re in need of a re-set, the resort’s spa (Halehouse), restoration (Springhouse), & movement studio (Fieldhouse), are ideal to unleash your untapped potential. With a focus on total wellbeing, each house creates individualized programs to balance your mind and spirit. 

As you head out of town, donʼt worry, a return visit is a must, not just because youʼve likely joined at least one wine club, but because thereʼs more than enough to see to justify a second, third or fourth trip.

WHILE HARVEST FROM AUGUST THROUGH OCTOBER IS TECHNICALLY “HIGH” SEASON FOR NAPA, THERE’S TRULY NO BAD TIME TO DRINK WINE.

THE LOGISTICS

While harvest from August through October is technically “high” season for Napa, there’s truly no bad time to drink wine. Temperatures are mild year-round and rarely go below 50 degrees during the day. In fact, we prefer spring, where the area’s already lushly green hillsides become even more vibrant with blooming flowers and plants coming into their own, as well as the quieter periods during the late fall and winter when you can avoid crowds at many of the larger wineries and feel almost as if you have the place to yourself.

We’d suggest spending a night or two on the front or back end of your visit in San Francisco. The newly-renovated Four Seasons San Francisco is a great choice for an easy and modern downtown location. It’s about a 90-minute drive out to Napa proper, longer if you’re headed up to areas like Calistoga, or hit weekend or rush hour traffic. While wine plus driving never mixes, we suggest renting a car for the duration of your visit, as having a car is useful to prowl between towns during the day. We love Silvercar, easily accessible from downtown San Francisco or the airport, as they rent only three fully-loaded Audi options: the A4, Q5 or Cabriolet, each equipped with navigation, fast passes for tolls and Wi-Fi to ensure a smooth trip. Oakland, Sacra- mento, Sonoma and San Jose airports are all options for easy connections within the state of California. Note that Napa County has a small airstrip reserved for private and charter flights.

When you’re in town, drivers are a must for full-day wine touring. Many hotels offer a house car option or their own recommended driver services. Just be sure to book in advance, as wineries and drivers alike book up weeks — if not months — in advance for weekend peak season experiences. While Uber is readily available, we found the wait for rides to belong and fares high compared to city prices.

This piece is adapted from its original format, written by McLean Robbins for Woodbury Magazine.

Itineraries

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Italy is the most-requested destination for Virtuoso travelers, and Lily Pond Luxury is no exception. Whether you’re planning your first visit or you live la dolce vita on the regular, find some of our favorite spots to stay, play, dine and wine in Tuscany, below.

Know Before You Go

Perhaps no area epitomizes la vera Italia more than Tuscany, with its rolling green hills, and quintessentially “Italian” small towns, or its beautiful bounty of cheese, wine, olives and more.  

Osteria di Passignano

Cooking school done right

But what many travelers forget is that Tuscany takes up much of central Italy, occupying nearly 9,000 square miles. That’s the size of New Jersey, or roughly the size of Israel… so planning your perfect visit requires a detailed vision for the scope and style of your travels.

Florence, the state capital and cradle of the Renaissance, is the area’s biggest draw, but you’ll find diverse and worthwhile terrain throughout the region, from the posh Forte dei Marmi to the beautifully preserved Siena, where the famous Palio horserace takes place every July and August.

But to truly enjoy Tuscany, it’s less a forced march through the Uffizi and Accademia with bits of wine and cheese thrown in for succor and more a leisurely stroll through small towns, with a great resort or villa as your home base.

For a city break/country escape, we love Castello del Nero, a 12th century restored castle turned 52-room hotel just 40 minutes south of Florence, on the outskirts of Chianti country, recently re-flagged under the wellness-oriented Como Hotels brand. The hotel offers regular shuttle service to both Florence and Siena, making a day trip possible, but not mandatory. Request suite 118, with its beautiful frescoes, or 116, with a gorgeously arched ceiling, or Room 222, which boasts a 30-square-foot rain shower with two showerheads.

While you’re in town, don’t miss a dinner or afternoon at the cooking school of Osteria di Passignano, an ancient monastery dating back to the year 395, established by the archbishop of Florence. Today, the Vallombrosan Order, a type of Benedictine monk, make excellent wine on the property. The Osteria also offers a cooking school, branded by KitchenAid, where guests learn to make traditional Tuscan fare, taste local olive oils, and, of course, sample local wine.

Il Borro

Convenient combination with Florence

Similar in vibe and proximity to Florence is Castello di Casole, a Belmond Resort, one of the largest private landholdings in all of Italy – if you’re traveling with kids, this is one of the more family-friendly high-end Tuscan options in the area.

Arguably one of the best names in Tuscan wine, Antinori is a must-stop and just an hour from Florence perfectly positioned on the highway toward Siena. You can taste your way through Chianti Classico in the impressive winery that’s been in the same family for 26 generations, since the year 1385. It’s well worth a seven-wine cru tasting, as well as lunch at the onsite Rinuccio 1180, where you’ll see 360-degree views of the surrounding countryside.

The resorts themselves are practically playgrounds for the epicurean-inclined, but for those who want something a bit more physical for their souvenirs,  plan for an afternoon The Mall, an outdoor outlet mecca with more than two dozen shops, including massive outposts of Gucci, Valentino, Tods, Dolce & Gabbana, Fendi and Prada, plus other top names including Loro Piana, Moncler, Jimmy Choo, Aquazzura and more. You’ll fight your way among tour busses on a weekend, but the sale prices are often worth the crowds. Goods are usually last season, not specialty “made for factory store” varieties. If it’s just Prada and Miu Miu you’re after, travel about an hour further afield for Space, located at the Prada factory, which boasts a dedicated outlet for clothing, shoes, and bags, plus an onsite café.

For honeymooners or those who wish to truly escape from it all, Relais Borgo Santo Pietro is another excellent option, a collection of fewer than 20 rooms and suites in a 13th century villa. Bohemian meets elegant, the resort looks straight out of an Instagram dream, with its picturesque walled gardens, infinity-edge pool overlooking vineyards, and its massive “white road” driveway lined with Cypress trees. For ultimate luxury, book one of the private villas with their exclusive use walled gardens or one of two brand new suites featuring private pools.

We spent part of our own honeymoon at this gorgeous escape.

Borgo Santo Pietro

Romantic, Perfect for Honeymooners

We loved the intimate Borgo Spa, which makes its own in-house products from the herbs and animals on the property, as well as the onsite cooking school and Michelin starred restaurant Meo Modo, which dishes up the modern farm to plate fare with a dignity one wouldn’t expect in a remote countryside resort. You’ll be walking distance (or a short Vespa) from the San Galgano Abbey, home of the famed Sword in the Stone, although if you spent days lounging by the infinity pool and never left the resort, we’d hardly judge.

If you’re headed afterward to Rome, look to Monteverdi, another high design escape that mixes traditional Tuscan with a stripped-down, minimalist modern aesthetic that could look Spartan, but instead manages to strike the perfect balance between luxurious and authentic.

Side Trips

With so much to see and do, it’s hard to say what to skip because even the small villages, such as the perfectly preserved Pienza, have their charm. It’s also possible to make an easy day trip to the walled city of Lucca, an excellent and less touristy alternative to Pisa.

To skip the true tourist traps, stay away from anywhere that actively advertises its status as a restaurant not catering to locals; photos of the food on menus or a “we ship to the States” sign are dead giveaways. Also, avoid anything billed as a “wine and cheese” tour, says Marco Amorico, of Access Italy, a celebrity favorite private tour company to Oprah, Ben Stiller, President Obama and a range of top executives, as they often serve a sub-par combination of both.

Be glad to know that all of our itineraries come with optional restaurant suggestions - we’re happy to book you a table at a Michelin-starred spot or a local eatery that suits your desires.

Tuscany’s vast size and often less-than- direct roads can make getting from point A to B a bit of a trek, but still, it’s worth heading deep into the countryside for a few days of rest and relaxation.

Uri Harash, who has been guiding well-heeled travelers around Italy for his company Perfetto Traveler since 2001, says that travelers often try to pack in more than they will enjoy. Spreading your time among three or four nights at several resorts is preferred to trying for several day trips from a city home base.

Florence Explorations

Pro Tip: Book Flytographer and rise before the crowds to capture the moment. This is us, back in 2017.

For a true Italian experience, it’s also strategic to plan your trip with ample time to relax and enjoy the Tuscan scenery. A great local guide can offer a “made in Tuscany” day to show you under-the-radar finds like an authentic producer of fine cashmere, or take you to goldsmiths or leatherworkers for a one-of-a-kind piece designed just for you.

You’ll save yourself hours of searching, and enjoy an authentic local expe-rience in the process.

When to Go

Tourist season begins in earnest on Easter Weekend and runs through September, but you can avoid crowds—and most costs—by visiting early or later in the season. July and August will bring the highest prices, and the biggest crowds. May, September, and even early October are some of our favorite times to visit Tuscany, as you’ll save cost and crowds but still have gorgeous weather.

Getting Around

While the romance of driving a convertible up and down the winding Tuscan roads or around the hairpin turns of Amalfi can seem a dream, but in reality, the unmarked roads, dust, traffic, and lack of cell service can make it a nightmare.

Private is the way to go – avoid the crowds and often unpredictable trains (except the high-speed versions between major cities like Florence and Rome) by utilizing private transfers and guides.

Whether you’re a first-timer or a regular visitor, maximize your time in Italy by planning for a minimum of three nights in each destination or hotel. While you may be tempted to go, go, go, skip daily guided touring for a mix of full- and half-day excursions, as well as plenty of downtime to enjoy local café culture, relax by the pool or beach club, or explore local towns and villages. 

An ideal length of the trip is anywhere from eight to 14 nights, with two to four destinations in total. Italy is also easily combined with other countries, including Greece, Monaco, France, or Switzerland.

Popular combinations in Italy include city breaks and country escapes such as Florence and the Tuscan countryside, Rome plus the Amalfi Coast, or even Tuscany and Amalfi together. Or, pair one of the destinations with an up-and-coming region, such as Forte dei Marmi, Sicily, Puglia, or Sardinia. For a family trip, try the grand tour, starting in Venice, meandering through Milan, finding fashion in Florence and then ending in Rome.

How to Get There

To begin in Tuscany, fly to Florence or Pisa, although Rome, with its direct flights, is also popular.

Even if you don’t intend to spend much time in the cities, you’ll find a night or two in Florence or Rome on the front or back end makes traveling that much easier – you’ll be easily primed for a morning return flight, and can get your quick fix of museums or designer shops.

Should you have several nights to spend in Tuscany, we’d suggest combining one or more resorts for an experience that spans several regions. In fact, for repeat visitors to the area or those staying at least a week, it’s worth considering a villa instead of a hotel for your stay.

We’re happy to source fully staffed villas for families or couples — our network extends throughout the country. These are often great options for longer stays.

Hotel de La Ville

Rome perfection

Even if you don’t intend to spend much time in the cities, you’ll find a night or two in Florence or Rome on the front or back end makes traveling that much easier, as you’ll be easily primed for a morning return flight and a quick fix of museums or designer shops. Of course, either of these destinations is worth a deep dive if you haven’t already experienced them to their fullest.

For a great Florence city center hotel, try the Hotel Savoy, a Rocco Forte property that just finished up a multi-year renovation this April. It’s a convenient location (just off the Piazza della Republica and right next to the Duomo) and the décor—the perfect blend of modern chic (think: chic Ferragamo-inspired paintings shoes) and historic (the property dates to 1893)—makes it a great escape.  The Lungarno property, owned by the Ferragamo family and right on the Arno, is another solid choice, as is the boutique chic Villa Cora, one of our favorites for honeymooners due to its intimate size and welcoming hospitality.

In Rome, an all-star is Hotel Eden, part of the Dorchester Collection. It’s perfectly perched on a corner in the via Veneto neighborhood, an area known for its spectacular views. Rocco Forte also boasts three great choices: Our favorite for location in Rome is the new Hotel de La Ville, near the Spanish Steps, or their all-suite Rocco Forte House.

This piece has been adapted from a story originally published in Woodbury Magazine by McLean Robbins.