Virtually every large-scale hotel in the Caribbean provides small sailboats (most often Sunfish, Sailfish, and small, one-masted catamarans) for its guests. For larger craft, the almost-ideal sailing conditions in the Virgin Islands and the Grenadines come instantly to mind. These two regions offer many options for dropping anchor at secluded coves surrounded by relatively calm waters. Both areas are spectacular, but whereas the Virgin Islands have more dramatic, mountainous terrain, the Grenadines offer insights into island cultures little touched by the modern world.
Other places to sail in the Caribbean include Antigua, Barbados, St. Martin, and the French-speaking islands. But if you plan on a lot of sailing, know that the strongest currents and biggest waves are usually on the northern and eastern sides of most islands -- the Atlantic (as opposed to the Caribbean) side.
- The Grenadines: Boating is a way of life in the Grenadines, partly because access to many of the tiny remote islands is difficult or impossible by airplane. One of the most prominent local charter agents is Nicholson Yacht Charters (tel. 305/433-5533, or 268/460-1530 from Antigua; www.nicholson-charters.com), headquartered in nearby St. Vincent. On Bequia, Mustique, Petit St. Vincent, and Union Island, all the hotels can put you in touch with local entrepreneurs who rent sailing craft.
- The British Virgin Islands: Perhaps because of their well-developed marina facilities (and those of the nearby U.S. Virgins), the Virgin Islands receive the lion's share of devoted yachties. The reigning capital for sailing is Tortola, the largest island of the British Virgins. On-site are about 300 well-maintained sailing craft available for bareboat rentals and perhaps 100 charter yachts. The largest of the Caribbean's yacht-chartering services is the Moorings (tel. 888/952-8420 or 284/494-2331; www.moorings.com). On the island of Virgin Gorda, in the British Virgin Islands, the best bet for both boat rentals and accommodations, as well as for a range of instruction, is the Bitter End Yacht Club (tel. 800/872-2392 in the U.S., or 312/506-6205; www.beyc.com).
- The U.S. Virgin Islands: Some of the biggest charter business in the Caribbean is conducted on St. Thomas, especially at American Yacht Harbor, Red Hook (tel. 340/775-6454; www.igy-americanyachtharbor.com), which offers bareboat and fully crewed charters. Other reliable rental agents include Charter Yacht League, at Flagship (tel. 800/524-2061 in the U.S., or 340/774-3944; www.vicl.org). On St. Croix, boating is less essential to the local economy than it is on St. Thomas or in the British Virgins, so if you're taking a Virgin Islands sailing trip, plan accordingly.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.