Caribbean Race Charters

You needn’t be a local or sail your own boat down to the islands to race in the typically warm and steady – well, yeah, sometimes blustery – trade winds of a Caribbean regatta and chill out further at the always maxi parties. Three big annual events in March and April – the St. Martin Heineken Regatta, the BVI Spring Regatta, and Stanford Antigua Sailing Week – have nonspinnaker charter divisions and the best (but not the only) access to a racing charter. Don’t tarry; you could easily miss the boat.

The race packages offered by The Moorings and Sunsail for the Heineken, BVI Spring, and Antigua regattas include entry fees, boat prep and measurement, a prerace briefing, and a race support staff. With all charter companies, expect to leave a higher (refundable) security deposit and, most likely, a larger (nonrefundable) yacht damage waiver fee.

Start your search for a regatta any time of year at or at Or cruise the Web sites of the events listed below, in order of appearance. All dates shown are 2009.

  • Southern Caribbean Regatta, includes the Carriacou Sailing Series (January 14 – 18;, Port Louis Grenada Sailing Festival (January 30 – February 3;, and Tobago Carnival Regatta (February 10 – 14;
  • Heineken St. Martin Regatta (March 5 – 8); Click on Race Info and then Charters. Plenty of information on this site.
  • Virgin Islands Race Week (March 27 – April 5). This combo 10-day event comprises the St. Thomas International Rolex Regatta ( and the three race starts of the BVI Spring Regatta and Sailing Festival (March 31, April 2, April 3 – 4); Click on Charter Options.
  • Stanford Antigua Sailing Week (April 26 – May 2); You’ll find a host of options for finding a boat to charter or a crew spot. Click on the Charter button.
  • Anguilla Sailing Festival (May 8 – 10); Charters for this low-key even are often available. To try for a crew berth, e-mail; write BOAT NEEDED in the subject line.
  • Ondeck Racing has all sorts of programs, from a whole skippered or bare boat to a spot on a crewed boat, for most of the regattas listed here. Check them out at

    A fleet of 10 identical Dragons will get their own start at Antigua Sailing Week. Contact if you’re interested in chartering one.

    Ambition Sailing books berths on a variety of boats for the Grenada, Tobago, Heineken, BVI, and Antigua events.

    Joining is free; members can post requests for crew spots or crew wanted.

    Most Read on Sail

    Also Popular on Sail


    Leave a Reply