Music festivals, regattas, cricket and carnivals - there's so much to do in a Caribbean season.

Carnival time

For crews with energy to burn, Tobago Carnival Regatta runs from 19-21 February. Tobago, 20 miles north-east of Trinidad, carries on the carnival spirit with a multifaceted Festival of Wind – races for yachts in various classes, plus local bumboats, windsurfers and kitesurfers, all braving the breezes off one of the Caribbean’s most photographed beaches, Pigeon Point. Anchor at nearby Store Bay.

ARC 09 - Heineken Regatta

OK, by now you’re acclimatised: you’ve partied a bit and you’ve raced a bit. So don your seven league boots and stride right up the island chain to be in St Maarten for the regatta that boasts the largest racing fleets and the most powerful parties in the Caribbean: the St Maarten Heineken Regatta, 4-7 March. Regularly attracting well over 200 boats, the event has classes for everything from beach cats to maxis, so every racer will find a niche. And the entertainment is world class. Again, there is an abundance of marinas and anchorages to choose from.

From St Maarten, slide off the wind for a ramble through the Virgin Islands, maybe catching a day of the Caribbean Arts & Crafts Festival, which runs from 5-10 March at Trellis Bay, Tortola – a prime ‘shopportunity’ for authentic Caribbean-made souvenirs and gifts. Anchor at Coral Bay on St John for the US Virgin Islands’ favourite annual music event, the St John Blues Festival, 17-21 March – the main concert is on 20 March.

ARC 09 - carnivalThen skip across to Cowpet Bay, St Thomas, for the International Rolex Regatta, 26-28 March. Grab a mooring off the St Thomas Yacht Club. Backtrack to Nanny Cay Marina, Tortola, for the BVI Spring Regatta, 2-4 April. These two major Caribbean regattas make up the prestigious Virgin Islands Race Week.

If camaraderie rather than competition is your style, the Caribbean’s foremost yacht rally, the Transcaraïbes, sets sail from Guadeloupe on 30 March and takes a fun-seeking fleet island and party-hopping all the way to a gala welcome in Cuba on 22 April.

  1. 1. Introduction
  2. 2. Jazz and blues
  3. 3. Carnival time
  4. 4. Iconic regatta
  5. 5. Head south for May
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