Key West Sailing Cruises and Charters

Our experience partners can take you on the adventure of a lifetime. Whether it's experiencing a romantic sunset cocktail sail or a sunrise excursion to the Dry Tortugas National Park, Stock Island Marina Village and our experience partners will deliver.

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Our Sailing Charter Experience Partners

BLUESAIL VACATION YACHTS & SAILING ACADEMY

Our motto is live, learn, explore. Experience unforgettable sailing yacht charters in some of the world's greatest destinations. Learn to sail, immerse yourself in the live-aboard lifestyle, and explore Key West aboard a Rogue Angel, Kaimana, Southern Crosser, and more. We offer day sailing, snorkeling, island hopping, and sunset cruise (upon request).

7005 SHRIMP ROAD, KEY WEST, FL 33040 | (813) 601-5243

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SAIL AWAY KEY WEST

Experience firsthand the wonder of an unspoiled tropical paradise right here in the Continental US. Sail to pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Keys. Whether you’re looking for activities on land or sea, our native Floridian staff can guide you as you plan a unique and customized getaway.

7005 SHRIMP ROAD, KEY WEST, FL 33040 | (305) 720-0896

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SUNSET SAIL KEY WEST

Enjoy a day sail or Key West's most elegant and exclusive sunset sail on this historic classic yacht. Built for General George Patton in 1939, When & If is open to the public for the first time in her history. Help raise sail, take the wheel, or sit back and relax with any adult beverages that you care to bring.

1939 WOOD SCHOONER | UP TO 28 GUESTS

202 WILLIAM STREET, KEY WEST, FLORIDA 33040 | (305) 587-4488

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TORTUGA SAILING ADVENTURES

Enjoy a private luxury yacht experience, and roam the aqua-colored waters of the lower Florida Keys archipelago as far out to the Dry Tortugas National Park. Guests can indulge in a variety of water sports activities, interact with an array of marine life, or just bask in the glow of a sunset with Tortuga Sailing Adventures.

7005 SHRIMP ROAD, STOCK ISLAND MARINA VILLAGE, KEY WEST, FL 33040 | (305) 896-2477

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DIESEL / $2.685