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Anguilla Vacations

Rapidly becoming a luxury destination with high-priced villas and upscale resorts, Anguilla, the most northerly of the British Leeward Islands, retains the laid-back character of a sleepy backwater. Goats still wander the streets and reggae music blares from passing cars.

Region: Caribbean

Featured Anguilla Hotel

Four Seasons Resort Anguilla

Four Seasons Resort Anguilla

Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

Experience the ultimate in refined luxury on a stretch of white sand beach, overlooking the clear blue Caribbean.

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What To See

Prickly Pear Cays
For the best diving on Anguilla, head out to this underwater cavern, where nurse sharks and barracuda swim through rock formations not far from several sunken shipwrecks. Snorkelling, diving and day trip tour operators leave out of Sandy Ground.

Shoal Bay East
You know that beach you picture in your mind's eye? The one where gentle trade winds waft your cares away and waves lap gently against your feet as you stroll the nearly deserted stretch of white sand? This is it.

Wallblake House
The Valley’s most interesting building is Wallblake House. Built in 1787, it’s the oldest structure on Anguilla and the only remaining plantation house on the island. Get a double dose of Caribbean history and check out the interior of the adjacent St Gerard’s church, which has a unique design incorporating a decorative stone front, open-air side walls and a ceiling shaped like the hull of a ship.


Bankie Banx's Moonsplash reggae festival is held anytime from late February to early April. But the big party in Anguilla is Carnival, a week-long festival that begins the weekend prior to August Monday (the first Monday in August). Get swept up in costumed parades, music and dancing, or celebrate the national pastimes of both boat-building and sailing with the locals as they buffet the waves in their fishing boats during Race Week, which is held at the same time as Carnival. In early November chill out with the international Tranquility Jazz Festival.