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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Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0!
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Set sail aboard our classically-styled schooner as she departs Key West's Historic Seaport for a full day of sailing and exploration through the  pristine waters of the Gulf of Mexico.
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The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.
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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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