Top Key West Cruises, Sailing & Water Tours

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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Take a tour from Miami to Key West, where you'll discover the most amazing underwater views on a glass bottom boat!
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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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Indulge your senses as you pass over natural sands through the blue waters of Key West into the playgrounds of wild dolphins on Dolphin Snorkel Sea Safari.
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Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins.
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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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Admire an exquisitely painted sky during this premium sunset cruise in Key West.
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Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun.
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This Key West experience lets you enjoy all that the island has to offer.
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Join us for Key West's Best Sunset Dinner Cruise.
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Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner!
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Watch the famous Key West sunset on a 1.5-hour catamaran cruise.
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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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This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to view the sharks.
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Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset.
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Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key West.
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See the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat tour from Key West!
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Picture the perfect Key West sunset, as you sail and sit on the deck of a romantic two-masted schooner.
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Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres.
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