Blending sumptuous resorts with low-key Caribbean charm, Anguilla is a paradise for travelers seeking to get off the grid without sacrificing luxury. Renowned as the culinary capital of the Caribbean, the secluded island offers five-star cuisine overlooking some of the most beautiful white sand beaches in the world – from which divers can explore centuries-old shipwrecks and expansive coral reefs amongst the local marine life.
Brilliantly white oceanfront hotels and villas contrast historic buildings and clapboard shacks, lending the island an authentic, easy ambiance not often found in luxury travel destinations.
And on the beach at Sandy Ground, the cultured tradition of boat racing draws spectators as locals race around the island – just 17 miles long by 3 miles wide.
Getting There
Tradewind Aviation flies scheduled one-hour flights to Anguilla from San Juan International Airport, as well as private charter flights from destinations throughout the Caribbean. New as of the 2023-2024 season, Tradewind will also offer scheduled flights from Antigua and St Barths directly to Anguilla between January and April 2024.
Best Time to Go
Ideal weather between mid-December and mid-April drives the high season, though flexible travelers can take advantage of lower rates as temperatures rise between May and August. Fall may be equally beautiful on the island, but many of the hotels and restaurants close down and hurricanes can affect travel plans with little notice.
Luxury Hotels and Private Villas
Image: Cap Juluca
Belmond Cap Juluca: Spanning 179 acres overlooking on Maundays Bay, Cap Juluca is unmistakable with its Moroccan-inspired villas (15 housing 69 guestrooms) and sense of romantic tranquility. The grand resort features many beautiful open-air spaces amidst its three restaurants, world-class spa, fitness center, and library. At the height of luxury, the Jonquil Suite highlights unparalleled ocean vistas and a private freshwater infinity pool.
Malliouhana: Perched on a lush coastal bluff on the western side of the island, Malliouhana offers luxury boutique accommodations in 44 stunning rooms and suites. The pristine beaches of Meads Bay and Turtle Cove are just steps from your retreat, where modern amenities blend with the warm, gracious charm of the Caribbean.
Zemi Beach House: Nestled on Anguilla’s tranquil in Shoal Bay with breathtaking ocean or garden views, guests staying at Zemi Beach are treated to their own little piece of the Island. This resort features the Thai House Spa, restaurants, bars, lounges and so much more.
Aurora Anguilla: Gourmet cuisine with Caribbean flair takes center stage at the sumptuous Aurora Anguilla. Nestled in the curve of Rendezvous Bay, the luxury resort features acclaimed restaurants, cooking classes, and wine tastings along with 98 suites and private villas, Venus Spa (try the aquatherapy), and an 18-hole championship golf course designed by Greg Norman.
The Villas: Anguilla is home to a number of spectacular villas, from extravagant retreats for 50 (Sheriva Estate) to getaways that set the stage for tranquil seclusion (Little Harbor Estate and Nevaeh, among others).
Click here to view Tradewind’s current partner experiences.
Authentic Caribbean Cuisine
Pimms: The elegant, columned dining room at Pimms at Cap Juluca offers some of the most delicious European and Caribbean fusion cuisine on the island. Indulge in Anguillan crayfish and other delicacies while enjoying the award-winning wine list and views of Maundays Bay.
Veya: For 10 years, Veya has been delighting palates with their self-dubbed cuisine of the sun. The acclaimed eatery features exotic flavors from around the world such as Chef Carrie Bogar’s grilled jerk spiced tuna and her tamarind glazed roast.
Jacala Beach Restaurant: In an open-air dining room overlooking the coastline, Jacala Beach Restaurant invites guests to dine on French cuisine in beautiful presentations, like olive oil poached mahi-mahi with curry-lemongrass sauce.
Image: da’Vida
da’Vida: Spectacular local and international fare come together at da’Vida, one of the island’s best beachfront eateries. The restaurant (and spa) has casual burgers, sandwiches, and wraps at the bar as well as elegant dinner menu items like ginger teriyaki sea scallops.
What to See and Do
Thirty-Three Beaches: Shoal Bay East is considered to be one of the most beautiful beaches in the world, and the other 32 beaches are well worth the visit too, from Meads Bay to Sandy Ground to Cove Bay.
Sailing and Other Watersports: Offshore cays and secluded shorelines are all within a short sailboat or glass-bottom boat ride, and make sure to bring your snorkeling and diving gear for the chance to see sea turtles, parrot fish, and blue tangs. With seven marine parks and nine shipwrecks, Anguilla is a diver’s haven (we recommend the underwater cavern Prickly Pear Cays), and you can also try your hand at kitesurfing, windsurfing, and fishing.
Historic Landmarks Meet Local Art: A walk through Anguilla’s small towns will lead you to a number of quaint art galleries, including Cheddie’s Carving Studio where you can shop for driftwood sculptures. History buffs will also enjoy exploring the island with destinations like the Wallblake House, the oldest structure on Anguilla built in 1787, and St. Gerard’s church, an open-air place of worship with a ceiling shaped like a ship’s hull.
Annual Traditions: Regattas, golf tournaments, seasonal festivals, and concerts on the beach define the annual gatherings on Anguilla, but most anticipated of all are the boat races held during spring and summer. Become a spectator at the Anguilla Day Round the Island Race in May or the Champion of Champions race, held at the end of Boat Racing Week in August, for a true taste of island culture.
*Featured Image: Cap Juluca