Key West Sailing Trips

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.
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Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge.
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Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness.
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This exclusive experience is for 1 to 40 persons as a private charter and includes unlimited pastries, juices, coffee and mimosas for your group!
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Join us for a snorkel adventure to the only living coral reef in North America.
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Join us for a snorkel adventure to the only living coral reef in North America.
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Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the waters of the Florida Keys.
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Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner!
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Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and snorkeling the perfect way to spend a fun day in the sun.
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Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner.
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Spend a beautiful Florida day out in the clear, blue waters on a snorkeling and dolphin-watching sailing excursion.
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The Solé Watersports Sunset Cruise at Hawks Cay Resort is the only Sunset Cruise in the Duck Key area.
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This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling and sailing!
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Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat.
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