While each island in the Caribbean boasts its own singular personality, many visitors agree that there’s something particularly special about Anguilla. Lined with 33 white-sand beaches and surrounded by shimmering turquoise waters, this sought-after British territory is a serene paradise where friendly Caribbean vibes meet barefoot luxury.
As one of the Caribbean’s most laid-back (yet upscale) destinations, there’s an effortless ambiance to the enclave, nestled near St. Martin and St. Barths and stretching just 17 miles long, three miles wide. Better yet, what it lacks in size it makes up for in charm: Anguilla is home to some of the Caribbean’s most coveted dining destinations, beachside resorts, and leisure experiences.
Here’s how to get to Anguilla, and the best ways to discover all that this welcoming Caribbean haven has to offer.
How to Get to Anguilla
Even as one of the region’s hidden gems, Anguilla is surprisingly easy to access via Tradewind Aviation. Tradewind offers regularly scheduled flights from December through April, departing from San Juan, Puerto Rico.
San Juan can be easily reached from the mainland by both commercial and private flights, and given its status as a U.S. territory, the customs and immigration process for American travelers is a breeze. After your arrival at the San Juan airport, a private lounge for Tradewind passengers awaits with refreshments and WiFi to enjoy before your journey to Anguilla. For an even more seamless travel experience, opt for VIP Experience to help facilitate a smooth transfer between flights.
For the 2023-2024 season, Tradewind will also offer scheduled flights from Antigua and St Barths seasonally between January and April 2024.
Serviced by a fleet of Swiss-made Pilatus PC-12s (featuring air conditioning, a pressurized cabin, and plenty of luggage space), unwind on your flight with complimentary snacks and refreshments including wine and beer before stepping into Anguilla’s salty, reinvigorating air.
For a more direct route, Tradewind private charter flights can also be arranged from the U.S., Puerto Rico, the U.S. Virgin Islands, and Antigua. (Longer journeys, such as from the mainland U.S., are offered on Tradewind’s fleet of Citation Jets.)
Where to Stay
Anguilla offers a host of luxe properties to call home during your Caribbean retreat. One of the island’s most iconic properties, the Belmond Cap Juluca, offers romantic, Moroccan-inspired décor and world-renowned service across 179 pristine beachfront acres. For a tropical boutique hotel experience, stay at Zemi Beach House, set on Anguilla’s famed Shoal Bay Beach and featuring the island’s celebrated Rhum Room.
Malliouhana is another favorite — this lush hideaway on the northwest corner of the island beckons with its modern glamour and spectacular views of Meads Bay. The sleek, sophisticated Four Seasons Resort and Residences Anguilla is also a chic option in the area, with its 181 accommodations brought to life by sought-after interior designer Kelly Wearstler.
Meads Bay is also home to Frangipani Beach Resort, an intimate boutique property boasting 19 luxuriously appointed rooms. Overlooking a stretch of pristine white sands and expansive turquoise waters, the property blends island adventure (think complimentary motorized and non-motorized water sports) with blissful relaxation.
Along the curve of Rendezvous Bay, the Aurora Anguilla also caters to high-end travelers. The resort is especially known for its gourmet persuasions (such as fine-dining opportunities, a hydroponic farm, and cooking classes), and it’s also home to the island’s only golf course, designed by Greg Norman.
Finally, housed in a tropical mansion with just nine suites, Quintessence Hotel (fondly known as The Q Hotel) offers a secluded escape into ultimate luxury.
Where to Dine
Lauded as the culinary capital of the Caribbean, Anguilla’s array of fine island dining outposts is second to none. In a lovely, light-hued setting in Belmond Cap Juluca, the romantic Pimm’s serves upscale takes on Caribbean dishes, while the resort’s Cip’s by Cipriani is the perfect destination for a fine Venetian lunch by the beach (best paired with a glass of crisp rosé).
Or, discover the meaning of “Cuisine of the Sun” at Veya, a highly rated island mainstay featuring a creative menu of Caribbean, Moroccan, and Asian cuisine from its treehouse-inspired perch. There’s also the acclaimed Jacala Beach Restaurant — though it’s adopted an unassuming online presence, it’s still considered one of the island’s top purveyors of French-influenced island fare.
For a more casual bite, head to the well-loved Straw Hat, featuring a seasonally driven and locally sourced menu within Frangipani Beach Resort. And because no visit to the Caribbean is complete without a visit to a charming beach hut, stop by the Sunshine Shack on Rendezvous Bay beach for a true taste of the local flavor.
What to Do
As gentle azure waves lap over pristine sands, there’s no question that Anguilla’s beaches are some of the best in the Caribbean. With 33 of them, it’s near-impossible to get your fill of each one on a single trip, but the spectacular Shoal Bay East can’t be missed — it’s often considered one of the most beautiful stretches of sand in the world.
Beyond the beach, there are plenty of opportunities to discover the colorful sea life brimming beneath the ocean’s surface with a scuba diving or snorkeling excursion. Other water sports, such as paddleboarding, kitesurfing, windsurfing, and fishing are also popular, though sailing may take the crown as the island’s favorite aquatic pastime.
Back on land, Anguilla offers an array of charming boutiques ranging from local craftsmanship to curated luxury. The island’s top resorts also offer uniquely serene spas, though the Zemi Thai House Spa may be the most spectacular — the 300-year-old Thai house is a holistically inspired sanctuary for rejuvenating treatments, elevated wellness offerings, and more.
Of course, the ultimate activity on Anguilla may just be, well, nothing. After all, there’s no better way to soak in the island’s relaxed splendor than dozing off under the sun while simply enjoying this slice of Caribbean paradise.
Tradewind Aviation runs regularly scheduled flights to Anguilla from San Juan, as well as private charters to and from Anguilla from the continental U.S., Puerto Rico, the U.S. Virgin Islands, and Antigua.