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Top May Caribbean Events

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Here are my picks for the top festivals and cultural events in the Caribbean during the month of May, including concerts, sports, sailing, and more.

Antigua Tennis Week

© Curtain Bluff
Hosted by the Curtain Bluff resort, this annual celebration of all things tennis includes demonstrations and clinics led by international tennis pros. The event has been held since the mid-1970s.

Grenada Drum Festival

Courtesy of the Grenada Board of Tourism
Organized by the Tivoli Drummers, based in the village of Tivoli in Grenada's St. Andrew parish, this annual celebration of Afro-Caribbean drum music includes concerts, food, parties, and cultural exhibits.

Curacao Dive Festival

With more than 60 dive sites all around the island, Curacao has developed a reputation as one of the Caribbean's top dive destinations. The annual Curacao Dive Festivals features dive workshops, films, social events, and of course guided dives every morning.

British Virgin Islands (BVI) Music Festival

Held in the village of Cane Garden Bay on Tortola, the annual BVI Music Festival is a relatively low-key gathering of reggae, steel pan, soca, and hip-hop artists. Special ferries run from St. Thomas to Tortola so visitors to the U.S. Virgin Islands can join the fun.

Foxy's Wooden Boat Regatta

© British Virgin Islands Tourist Board
Foxy's resort in the boating-mad British Virgin Islands has sponsored an annual Wooden Boat Regatta for more than three decades, although a race for older fiberglas-hulled boats was recently added as wooden boats become ever scarcer. The event at the Jost Van Dyke bar includes a party with live music, and if you indulge too much while watching the races you're always welcome to sleep it off on the beach.

Antigua & Barbuda Sports Fishing Tournament

Cash prizes are offered to participants in this long-running fishing tournament that includes a marlin division and prizes for successful landings of tuna, wahoo, dolphin, and king fish. And of course lots of eating, dancing and drinking at local establishments like the Life Bar & Restaurant, Mia Cucina, and the Copper and Lumber Hotel.

Cayman Islands Carnival (Batabano)

© Cayman Islands Department of Tourism
Originally a celebration of turtle fishing ("batabano" is a term that refers to the tracks left by turtles as they move across the sand), the Cayman Carnival Batabano today features costumed parades ("mas") for both adults and children as well as street parties and evening events.

St. Lucia Jazz Festival

Performers light up the main and "fringe" stages as this annual celebration of jazz music; the lineup tends to stick to various forms of jazz and R&B, unlike some other "jazz festivals" where other genres of music seem to outnumber the jazz musicians. Shows are held throughout St. Lucia, including the towns of Castries, Soufriere and Vieux Fort and the village of Laborie. The main venue is in Gros Islet, at the pier on Pigeon Island.

Barbados Gospelfest

© Barbados Gospelfest
The Caribbean's leading showcase for international, regional and local gospel talent features bands and singers from around the world. This family oriented festival is held at venues throughout Barbados over a week in mid-May; some events are free, some charge a fee.

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