Itineraries

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

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. 

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. 

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. 

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. 

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. 

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 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. 

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.