Photo Credit: Etolane

Although there always seems to be a party going on at Anguilla’s numerous beach bars, the island’s biggest celebration is the Anguilla Summer Festival, the island’s answer to the lively Carnival celebrations which take place throughout the Caribbean. Music, dancing, and boat racing are the most common activities during most festivals, but the island’s national sport is the main focus of the three day Anguilla Regatta.

ABC Flower and Garden Show

The ‘ABC’ host of this late February floral exhibition is the Anguilla Beautification Club, which judges floral displays from the island’s most talented gardeners and vegetable growers. Prizes are given for student art, student miniature gardens, best vegetable gardens, and best home gardens.

Moonsplash Reggae Festival

For more than 15 years, famed Anguillan reggae artist Bankie Banx has hosted this annual reggae festival at Rendezvous Bay’s Dune Preserve at the end of each March. The event consists of two days of lively performances by some of the world’s finest reggae musicians followed by an even livelier beach bash at Dune Preserve.

Festival del Mar

Each April, Anguilla honors its maritime heritage with this festival dedicated to the sea. Competitions in triathlons, seafood cooking, fishing, swimming and boat racing all play an important part in this popular Island Harbour event, which also features dry land activities such as volleyball and concert performances.

Anguilla Regatta

Sandy Ground hosts the biggest and best known of Anguilla’s many boat races during three fun filled days in the middle of March. Not only do visitors get to watch Anguilla’s finest race to the finish during this celebration of the island’s national sport, but they can also party the night away at one of Sandy Ground’s bustling beach bars. All of the regatta’s proceeds go towards the Anguilla Youth Sailing Club, which has taught the sport to more than 400 of the island’s most talented young sailors over the years.

Anguilla Summer Festival

Like most Caribbean islands, Anguilla celebrates its own vibrant Carnaval between the months of July and August. This Anguilla holiday's loudest and liveliest event is J’ouvert, a giant street party beginning at the crack of dawn and lasting until noon. J’ouvert participants follow live soca and calypso bands down the streets until the parade ends with a massive beach party. The Miss Anguilla Queen Pageant and Swimsuit Competition winners are crowned during the island’s largest event, and other activities include boat races and calypso contests.

Tranquility Jazz and Golf Festival

Each November, the Temenos Golf Club and CuisinArt Resort and Spa host this annual celebration of music and the putting green. After golfers finish their challenging Temenos Course rounds each day they head to the lawn for nightly jazz performances to relax. Some of Anguilla’s smaller beach bars have also begun hosting jazz performances of their own.

Anguilla Optimist Race Against AIDS

The Anguilla Optimist Youth Club hosts this annual race to raise awareness and support for AIDS treatment and research prior to International World AIDS Day in November. Participants can choose to run, jog, or simply stroll during the race’s half marathon, 10 km, or five kilometer runs.

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