Anguilla has all the hallmarks of a perfect tropical getaway: the beaches, the palm trees, the luxury resorts. But regulars who come to this British overseas territory in the Caribbean know there’s more to the oasis than meets the eye. Packed into just 35 square miles of paradise are epicurean restaurants, lively bars (boasting a serious local music scene), and did we mention the fabulous people? This is a place with personality and style, where the community is so welcoming and the culture so creative that it only takes a few days before you’ll feel like a local. Its 30-plus beaches are among the Caribbean’s finest, but you’ll never mistake any of it for St. Barts or Barbados. Because Anguilla marches to the beat of its own drum, never pretentious, always original, and forever an island to call home away from home. Here’s how to do it right in one perfect long weekend.
9 AM: Life’s a Beach
First things first: Hit the beach. There’s one for every kind of visitor. Shoal Bay’s pink sands stretch for two miles, and its calm waters protected by a coral reef make it the perfect swimming spot for families. Lively Sandy Ground is home to brown-sugar sand and some of the island’s liveliest bars and restaurants. For a prime spot with five-star service, look no further than Barnes Bay Beach in front of the Four Seasons Resort and Residences Anguilla. The hotel’s Half Shell Beach Bar is right on the sand, serving fruity Anguilla Slings and local favorites like grilled crayfish and conch fritters.
1 PM: Take a Hike
If you can drag yourself away from the sand, take advantage of Anguilla’s rugged eastern coast with a trek beginning at Windward Point Bay. The rocky landscapes are a great place to spot soaring pelicans and the native red-crowned melon cacti. The climb to the top is challenging—but easy enough for hikers of all level—and the reward at the top is always worth the effort. The panoramic views stretch all the way to St. Barts.
4 PM: Say Ahhhh
Soothe those hard-working muscles with a treatment at the Four Seasons Spa. The Double Rainbow treatment—named for Anguilla’s moniker as the Rainbow City of the Caribbean—offers twice the relaxation, with an esthetician performing the Sea of Life facial while a second therapist revives the legs and feet with a deep-tissue massage.
6 PM: Expand Your Horizons
They call it the Sunset Lounge for good reason: The Four Seasons’ open-air bar overlooking Barnes Bay is legendary for its westward facing views. And the cocktails are just as colorful. Try the Passionate, with seven-year-old rum and passion-fruit amaretto foam, or the Sundown Elixir, made from jasmine vermouth, peach schnapps, lychee, and St. Germaine.
8 PM: Spice up the Night
Make it a festive first night and head to Picante’s, the island’s legendary Mexican restaurant known for its stiff drinks and spicy dishes. The colorful eatery’s party vibe makes it almost too easy to pair those carnitas tacos with another round of ‘ritas (and another...and another).
8 AM: Island Energy
Seize the day with some al fresco activity while the early morning breezes are still blowing. Head to an outdoor yoga class on Barnes Bay Beach, conquer the climbing wall at the Four Seasons Sports Pavilion, or visit the Sea Centre to hit the water via kayak, stand-up paddleboard, boogie board, or windsurfer (all complimentary!).
9 AM: Sail Away
Grab a healthy morning smoothie at the Half Shell Bar on your way to meet the Four Seasons’ pleasure cruiser for a day of bay hopping around the island. The resort’s 38-foot bow rider sails to some of Anguilla’s most idyllic and remote spots, including Prickly Pear, a pair of small uninhabited islands, and Little Bay, an isolated cove where daredevils can jump on a cliff into the sparkling waters below.
2 PM: Retail Therapy
Back on dry land, have your Exclusive Resorts Concierge arrange a car to the island’s top boutiques for an afternoon of shopping at boutiques like Why Knot?, Fabiana Liburd’s Crocus Bay mecca of beachwear and coverups (J. Lo and Beyonce are reportedly fans). Don’t miss Irie Life—with locations in Sandy Ground and South Hill—for not-so-average souvenirs and beachy attire. And stop by Cheddie’s Carving Studio for driftwood and other natural-wood sculptures to take home.
7 PM: Divine Dining
All that shopping sailing works up an appetite. Head to Cip’s, the new fine-dining hotspot at the Cap Juluca, a Belmond Hotel. The restaurant’s views are unmistakably Caribbean, overlooking pristine Maundays Bay, but the dishes will transport you straight to Italy, with favorites like pumpkin risotto, fresh ricotta agnolotti, and carpaccio clássico all inspired by the menu at Cipriani, Belmond’s legendary Venetian hotel.
9 PM: Soca ‘Till Dawn
Anguilla is, at its heart, a musical island. Catch the local sound at Bankie Banx’s Dune Preserve, the Rendezvous Bay bar owned by one of Anguilla’s most famous musicians, Bankie Banx. The beats are always flowing (as is the rum) and on weekends, expect a live show that’s bound to get you dancing the soca like a pro.
11 AM: The Most Important Meal
Sleep in and meet the brunch crowd at Tasty’s, where chef-owner Dale Carty is regarded as an island celebrity. The turquoise-and-lilac ambiance is sure to brighten your morning, as are Carty’s saltfish cakes—they’re famous among Anguillians.
2 PM: Apron Up
You’ve tried the local delicacies—now try your hand in making them yourself, with a private cooking class in your villa. Let your Exclusive Resorts Concierge arrange a chef-lead and friendly-for-the-whole-family session, where you’ll learn the secrets of making delicious Johnny Cakes (an island staple made from fried flour and cornmeal) and fresh ceviche.
3 PM: The Perfect Ending
Forget itineraries, cancel the rest of your plans, and stay in your villa. Laze by (or in!) the pool until dinner, when one of the Four Seasons chefs arrives with fresh catches to grill up along with crab coconut rice, jerk-roasted potatoes, or conch chowder. The private family feast is the ultimate way to end a perfect long weekend in magical Anguilla.
The Exclusive Resorts homes at the Four Seasons Resort and Residences Anguilla are beach living at its finest. The Club’s four four-bedroom villas—each with its own private pool—were recently renovated to reflect their pristine surroundings and the hotel’s chic Kelly Wearstler–designed aesthetic. Whether you’re dining on the rooftop terrace, sunning by the pool, or reading on your balcony, the views of the crystalline Caribbean Sea are always front and center. The Four Seasons is a destination in its own right, with three restaurants, two beaches, three pools, a watersports center and kids’ club, and an on-site COVID testing center. The resort is centrally located to all of Anguilla’s top restaurants and attractions.