David Schmidt had an exciting time at the Culebra Heineken International Regatta ("El Dragón," page 54), but Caribbean regattas aren't the sole province of locals and sailing journalists. Three big ones—the St. Martin Heineken Regatta (early March), BVI Spring Regatta and Sailing Festival (early April), and Antigua Sailing Week (late April)—have charter (no-spinnaker) divisions, and several charter companies allow their boats to enter. (Note that many charter companies do not; others do, but don't have this information on their Web sites, so it will pay to call around.) The Moorings and Sunsail both offer racing packages that include entry fees, boat prep and measurement, and race support. Sunsail will also arrange charters for smaller regattas, such as Angostura Tobago Sailweek, that take place near one of its bases. Neither guarantees a private meeting with the "dragon."
The über Web site for Caribbean racing events is www.caribbean
racing.com; start here to find an annual calendar of events. Your basic choices are to charter a bareboat or to take a slot (or slots, if your friends want to join you), on a privately owned boat that comes with a captain and, usually, one crew. You'll find lists of charter companies (presumably all willing to do race charters) and private boats on the St. Martin Heineken site, www.heineken
regatta.com; the Antigua Sailing Week site, www.sailingweek.com; and the BVI Spring Regatta site, www. bvispringregatta.org. The BVI event has the additional option of chartering an IC24 (a converted J/24) from Racing in Paradise (www.racinginparadise.com) for a reasonable $1,700/week; you'll have to arrange shoreside accommodations, of course (and make your charter arrangements early; this is an active, locally owned fleet). I saw on these Web sites a potential third option—namely, crew slots on boats available through various European organizers.
If your objective is racing in Caribbean conditions rather than participating in a specific regatta, the Bitter End Yacht Club on Virgin Gorda has two big events, the Pro Am (early November) and the Midwinter Regatta (small boats, early January). Both are open to resort guests, as are the Sunday-morning Laser races and Wednesday-afternoon beer-can races, and you won't have to do any cooking.
Florida Yacht Charters (www.floridayacht.com) does allow charterers to participate in regattas and suggests a couple of "fun" races in South Florida—the Columbus Day Regatta (Rickenbacker Causeway to Elliot Key) and the Miami–Key Largo Regatta (mid-April)—as well as Abaco Race Week, Bahamas (early July).
Even if you don't consider racing to be a spectator sport, some races are—especially the colorful regattas that involve native boats. Here are some that can be watched while on a charter, and there's no yelling (on your boat): Exuma Family Island Regatta, George Town, Exuma, Bahamas (native sloops, April); Annual Grand Bahama Island Sailing Regatta (native sloops, June); Port Louis Grenada Sailing Festival and Workboat Regatta (late January); Foxy's Wooden Boat Regatta, Jost Van Dyke, BVI (late May).