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

BLUE OCEAN CHARTERS

Blue Ocean Yacht Charters (BOYC) makes all your yacht charter dreams come true. BOYC specializes in overnight private yacht rentals at the marina, as well as day excursions, multi-day charters, or stand-alone day excursions. Choose from a 4 hour or 8 hour luxury cruise where you can relax under a sunset sail, learn to sail, snorkel to a shipwreck, swim, fish, catch lobsters (seasonal), tour key west and take in the historic landmarks ocean-side.

(305) 923-4152

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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).

(813) 601-5243

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FLORIDA YACHT CHARTERS

Florida Yachts Charters is a boutique yacht charter company offering the world’s top brands of sailing yachts, catamarans, and power boats. We partner with Atlantic Cruising Yachts, and offer several sailing certification courses as an affiliate of the American Sailing Association as well as private powerboat instruction. Private, semi-private, or group lessons to get certified to bareboat charter around the world is also available to you.

(800) 650-6940

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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.

(305) 720-0896

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SUNSET SAIL KEY WEST

Enjoy a day sail on Key West's most elegant and exclusive sunset sail on this historic, classic yacht, Conch West, which is docked right here at Stock Island Marina Village. With great local captains and crew, and the pristine waters of the Florida Keys at our disposal, we're confident that we'll have everything you need to make your dream sail come true. Plus, seasonally you’ll also be able to experience the schooner When & If, built for General George Patton in 1939. Help raise sail, take the wheel, or sit back and relax with any adult beverages that you care to bring.

(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.

(305) 896-2477

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DIESEL / $2.685