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Compare boat and sailing experiences by itinerary, duration and departure arrangements. Read the individual inclusions to distinguish sightseeing trips from experiences with meals or activities.
Explore experience ↗◷ 2 hr
Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well b
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Explore experience ↗◷ 1 hr 45 min–2 hr
Step aboard the Pride of Key West, the island’s only Glass Bottom Boat. This family-friendly tour invites you to explore North America’
From $64.13 USD
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Explore experience ↗◷ 1 hr 30 min
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy
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Explore experience ↗◷ 10 hr
Explore beautiful tropical beaches on this full-day catamaran trip from Key West to Dry Tortugas National Park. The Dry Tortugas island
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Explore experience ↗◷ 50 min
Fury’s Key West Parasailing offers an exhilarating way to experience the stunning beauty of Key West from the sky. This unique adventur
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Explore experience ↗◷ 2 hr
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West
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Explore experience ↗◷ 3 hr
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both
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Explore experience ↗◷ 2 hr
Come see for yourself why Marathon Mermaid is voted the #1 thing to do in Marathon! Watching the sunset by water is a must-do when visi
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Explore experience ↗◷ 3 hr
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an
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Explore experience ↗◷ 3 hr 30 min
Picture yourself aboard our unique tiki boat, the Lazy Lady, cruising through the crystal-clear waters toward a secluded sandbar. The s
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Explore experience ↗◷ 1 hr 30 min
Get ready for an unforgettable journey that takes you through the natural beauty of Key West’s surrounding waters. Our Craigcat boat to
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Explore experience ↗◷ 2 hr
“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West p
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View datesHook your night with Key West’s best live music spots, from sunset sets to Duval’s after-dark pulse, before the real surprise begins.
Compare Key West sunset dinner cruises by meal style, atmosphere, duration, and inclusions, with practical advice for choosing and booking the right evening.
Best Key West sunset cruise picks reveal which boats, vibes, and hidden extras turn an ordinary evening into something you won’t expect.
