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The line has a fleet of five sailing ships plus one freighter and a supply ship (Amazing Grace). Most cabins have bunk beds and private facilities, but not much beyond that. Shorts and beachwear is the full-time dress code. There are not any casinos or any type of organized entertainment aboard. Passengers could participate in operating the sails if they wish so. Absolutely fabulous Caribbean itineraries. Windjammer Barefoot Cruises, still a family-run company, was founded in 1947 by Captain Mike Burke. He took a dilapidated 70-foot ketch and began offering ultra-informal trips to the Bahamas. The company is based in Miami. In the Windjammer fleet of sailing ships, the 72-passenger Mandalay, built in 1923, is its most venerable. Other ships in the line include the 64-passenger Yankee Clipper (1927), 74-passenger Flying Cloud (1935), 126-passenger Polynesia (1938), and 120-passenger Legacy (1959). Those are the years when the ships are built, not their last refurbishment. The 94-passenger Amazing Grace is a world of its own; the freighter ship provides the sailing ships with supplies and offers two-week-long cruises.

Windjammer Barefoot Cruises offers a limited number of shipboard positions, mostly deck hands, stewards, cooks.

Tall ships and itineraries:

Amazing Grace: 96 passengers, 234 ft. Itineraries: Caribbean, Central America (Great Inagua, Grenada, Iles des Saintes, Jost Van Dyke, Little San Salvador, Nevis, Norman Island, Palm Island, Plana Cay, St. Kitts, St. Barts, St. Lucia, St. Maarten, Tortola, Trinidad, Virgin Gorda).   Amazing Grace cruise and supply ship
Flying Cloud: 78 passengers,208 ft. Itineraries: Caribbean (Cooper Island, Jost Van Dyke, Norman Island, Peter Island, Salt Island, Tortola, Virgin Gorda).   Flying Cloud - sailing cruise ship
Legacy: 122 passengers,294 ft. Itineraries: Caribbean (Puerto Rico, Culebra Island, Jost Van Dyke, St. Croix, St. John, St. Thomas, Norman Island, Virgin Gorda).   Legacy tall ship
Mandalay: 72 passengers, 236 ft.. Itineraries: Caribbean (Antigua, Bequia, Carriacou, Dominica, Grenada, Iles des Saintes, Martinique, Mayreau, Nevis, Palm Island, St. Lucia, St. Vincent, Tobago Cays).   Mandalay tall ship
Polynesia: 126 passengers, 248 ft. Itineraries: Caribbean (Anguilla, Nevis, St. Kitts, Saba, St. Barts, St. Eustatius, St. Maarten, Tintamarre).   Polynesia tall ship
Yankee Clipper: 65 passengers, 197 ft. Itineraries: Caribbean (Bequia, Canouan, Carriacou, Grenada, Mayreau, Palm Island, St. Vincent, Tobago Cays, Union Island).   Yankee Clipper tall ship
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