From one-day jaunts to weeklong island-hopping cruises, the Caribbean is full of sailboat adventures. Island Windjammer Cruises and Windstar Cruises offer luxury Caribbean sailboat cruises. Windjammer Cruises sails a 101-foot schooner with an on-deck dining area, room for lounging and six double-berth cabins. Windstar's three ships have impressively large sails towering over vessels that cater to a limited number of guest. Visitors will find on-board dining rooms, sundecks, casinos, pools and entertainment areas. If you're interested in a quick sunset cruise or day-long island cruise, nearly every Caribbean island has a sailboat tour operator. Book these cruises upon arriving at your destination.
Chartering a sailboat provides all the benefits of owning your own luxury sailboat without the chores of sailing, cooking and cleaning. Sail Oasis provides dozens of charters in the Caribbean, and destinations include St. Lucia, Martinique and Grenada. Sail Oasis provides the sailboat, the crew and all the services of a hotel while you ply the Caribbean Sea. Almost all Caribbean Islands offer some type of sailboat charter service, whether from an international company or a local establishment docked near the marinas.
If you have never raised a mast, secured a boom or tacked, and you're not even sure what that means, then you need some training and a nautical dictionary. Steady winds, calm seas and exotic destinations make the Caribbean an ideal choice for attending sailing school. The School of Ocean Sailing, based in the Virgin Islands for the winter, offers sailing lessons aboard the SAMANA, a 52-foot ketch. Your classroom is the boat and the sea. Seven-day courses teach open-water sailing, theory and navigation. Other Caribbean sailing schools include Colgate's Offshore Sailing School and Sea Dog Sailing.
Perhaps you are already an experienced seaman and looking for a Caribbean sailing experience; a bareboat charter should serve your wishes. A bareboat charter means you rent the sailing vessel, but you are on your own for the itinerary, food and good times. Most bareboat charters come from private owners who list their vessels with charter companies. Barefoot Yacht Charters has a fleet of sailboats in Grenada, the British Virgin Islands and St. Vincent. Sailboats range from 32 to 51 feet, and are categorized as "luxury" or "value." Other bareboat charters in the Caribbean include Ed Hamilton & Co. and Sunsail Yacht Charter & Flotilla.
