Key West Sunset Cruises

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.
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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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Watch the famous Key West sunset on a 1.5-hour catamaran cruise.
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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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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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Join us for Key West's Best Sunset Dinner Cruise.
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This Caribbean-themed trip offers two bucket list items that Key West is famous for - a tropical coral reef and amazing sunsets.
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Key West Sunset Cruise with Live Music, Unlimited Beer & Wine.
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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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Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat.
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Enjoy this 3 hour sunset combo trip.
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The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.
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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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