Top USA 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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Get the total Miami experience with a bus tour of the city’s top interest points and icons followed by a Biscayne Bay cruise along Millionaire’s Row.
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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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Not only are we open (as of November 19, 2020), we are one of the best outdoor activities to do in San Diego.
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Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater!
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This Key West experience lets you enjoy all that the island has to offer.
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A three hour tour you won't want to miss!
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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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Sail the majestic Na Pali Coast and witness its beauty with 4,000-foot cliffs, cascading waterfalls, sea caves, secluded beaches, dolphins, turtles and breathtaking scenery.
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Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows.
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Exclusive to Sea Maui, it's the only sail that departs Ka'anapali beach 3 times a week with awesome LIVE music on board.
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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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What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life?
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Sail the legendary Na Pali Coast aboard Leila, a 50-foot Kauai-made sailing catamaran and witness the beauty of 4000-foot cliffs, cascading waterfalls, sea caves, secluded beaches, dolphins, turtles, and breathtaking scenery; all of which make Na Pali known as the jewel of Hawaii and the 8th wonder of the world.
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Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise!
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