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 has a popular summer festival that incorporates elements of Carnival as well as good old summer fun!
Hosted by Anguilla reggae legend and self-proclaimed "Kind of the Dune" Bankie Banx, Moonsplash is held each February at the funky Dune Preserve on Rendezvous Bay. This annual three-day music festival has attracted a diverse array of performers to its ramshackle stage over the years, including Steel Pulse, Third World, Inner Circle, Buju Banton, Toots & The Maytals, Jimmy Buffett, and John Mayer. The festival is low-key even by Caribbean standards, a sort of cultural counterpoint to Anguilla's tony hotels and upscale enclaves: think bars and buildings made of driftwood, blissed-out revelers lounging on the beach all night, and world-class music performed in the unlikeliest of settings.
Boating-mad Anguilla holds its annual regatta each May, and the four-day event includes a variety of beach parties as well as races between spinnaker, non-spinnaker, monohull, and multihull sailboats. All proceeds from the regatta go to benefit the Anguilla Youth Sailing Club. Spectators can view the races from some of Anguilla's most popular destinations, including Rendezvous Bay, Maunday's Bay, Mead's Bay, and Road Bay.
Anguilla's answer to Carnival runs over several weeks in July and August and combines typical road marches, pageants, and concerts with other summer fun activities, like a weekly beach party each Monday in August and a series of boat races. The result is that you'll never be bored, day or night, even when visiting Anguilla during the typically slower summer season.
Easter Festival del Mar
On Anguilla, the bounty of the sea has always surpassed that of the land, which helps explain the island's rich fishing and boating culture. Each Easter, the island's Festival del Mar celebrates this history with boat races (both full-size and model!), a fishing tournament, swim races, a traditional cooking competition, crab races, and of course concerts, food, and plenty of drink. The festival is centered on the (usually) sleepy fishing village of Island Harbour on the east end of Anguilla.
Anguilla has an interesting history, including an unhappy period where island residents chafed under administrators based in nearby St. Kitts. In 1967, a local uprising resulted in 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 an overseas territory of the U.K., but island residents still celebrate their 1967 revolution on Anguilla Day, May 30, when they at least achieved a greater degree of autonomy, if not outright independence.
As with just about any Anguillan celebration, Anguilla (AXA) Day features a boat race, in this case, the Round-the-Island race beginning and ending in Sandy Ground, with music and partying to end the day. Even if you don't have a boat you can join the fun with a band of "land racers" who follow the progress of the boats around the island in their cars.