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 non-spinnaker charter divisions, and several charter companies allow their boats to enter.
You should know that many charter companies do not allow their boats to be raced, while others encourage the practice. The information may not posted on their web sites, so call your favorite company.
Both the Moorings and Sunsail offer racing packages that include entry fees, boat prep and measurement, and race support. Sunsail will also arrange charters for smaller regattas that take place near one of its bases, Angostura Tobago Sailweek, for example.
The ber web site for Caribbean racing events is caribbeanracing.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 web sites of these tried and proven events:
St. Martin Heineken Regatta: heinekenregatta.com
Antigua Sailing Week: sailingweek.com
BVI Spring Regatta: bvispringregatta.org, where you have the additional option of chartering an IC24 (a converted J/24) from Racing in Paradise (racinginparadise.com) for a reasonable $1,700/week. You will have to arrange your own shoreside accommodations. 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 (floridayacht.com) allows charterers to participate in regattas and suggests a couple of "fun" evemts 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 Caribbean native boats. Here are some that can be watched from your own boat or 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 Bahamas 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).
Posted June 25, 2008