Must-See Events and Festivals in Anguilla

Music and boating are essential parts of Anguilla culture and are sure to be part of almost any major celebration on the island. Moonsplash is the most famous music festival on Anguilla and one of the best in the Caribbean, but the island also boasts a popular summer festival that combines elements of Carnival with good old summer fun!

Moonsplash

moonsplash anguilla
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Hosted by Anguilla reggae legend and self-proclaimed “King of the Dune” Bankie Banx, Moonsplash takes place each February at the funky Dune Preserve on Rendezvous Bay. This annual three-day music festival features a diverse array of performers drawn to its ramshackle stage, including Steel Pulse, Third World, Inner Circle, Buju Banton, Toots & The Maytals, Jimmy Buffett, and John Mayer. The festival’s atmosphere is laid-back even by Caribbean standards, creating a cultural counterpoint to Anguilla’s upscale hotels and enclaves: picture bars and buildings made of driftwood, blissed-out revelers lounging on the beach all night, and world-class music performed in the most unexpected settings.

Anguilla Regatta

Racing Sailboats in Anguilla
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Boating-mad Anguilla holds its annual regatta each May, featuring a four-day event filled with beach parties and races among spinnaker, non-spinnaker, monohull, and multihull sailboats. All proceeds from the regatta support the Anguilla Youth Sailing Club. Spectators can watch the races from some of Anguilla’s most appealing destinations, including Rendezvous Bay, Maunday’s Bay, Mead’s Bay, and Road Bay.

Summer Festival

Anguilla Summer Festival
Anguilla Summer Festival

Anguilla’s answer to Carnival stretches over several weeks in July and August, combining traditional road marches, pageants, and concerts with summer fun activities, including a weekly beach party each Monday in August and a series of exciting boat races. Therefore, visitors will find it nearly impossible to feel bored, whether day or night, during a trip to Anguilla, even in the typically slower summer season.

Easter Festival del Mar

Caribbean, Antilles, Anguilla, Upper Shoal Bay, fishing boats and shore
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On Anguilla, the sea’s bounty has traditionally outshone that of the land, explaining the island’s rich fishing and boating culture. Each Easter, the island hosts the Festival del Mar, which celebrates this heritage through exciting boat races (both full-size and model!), a fishing tournament, swim races, a traditional cooking competition, crab races, as well as concerts, food, and plenty of drinks. The festival is centered around the (usually) sleepy fishing village of Island Harbour on the east end of Anguilla.

Anguilla Day

Anguilla flag waving in the blue sky
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Anguilla has a fascinating history, including a challenging period when its residents felt oppressed under administrators based in nearby St. Kitts. In 1967, a local uprising led to the expulsion of Kittitian police and the brief (1967-69) establishment of the Republic of Anguilla. Ultimately, Anguilla returned to the British Empire and remains a British Overseas Territory. Nevertheless, residents continue to celebrate their 1967 revolution on Anguilla Day, May 30, a day that commemorates the achievement of greater autonomy, if not outright independence.

As is usual for any Anguillian celebration, Anguilla (AXA) Day features an exhilarating boat race, specifically the Round-the-Island race starting and ending in Sandy Ground, alongside music and festivities to conclude the day. Even if one doesn’t own a boat, joining the excitement is possible through a group of “land racers” who follow the boats’ progress around the island in their cars.

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