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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 ↗◷ 4 hr
We are Key West's largest boat rental service and have been helping travelers explore our local waterways for over 39 years. Our boats
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Explore experience ↗◷ 4 hr
Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your
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Explore experience ↗◷ 4 hr
Explore the vibrant waters of Key West on this 4-hour dolphin watch and snorkeling tour aboard a luxurious catamaran. Encounter playful
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Explore experience ↗◷ 3 hr
This three-hour private Key West dolphin safari combines wildlife searching with the flexibility of a private boat charter. Rather than
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Explore experience ↗◷ 8 hr
Explore the stunning Dry Tortugas National Park with a private boat charter tailored just for you. Departing from Key West, enjoy a ful
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Explore experience ↗◷ 4 hr
This private Key West snorkeling charter avoids the fixed schedule and crowds of a large group boat. The captain selects suitable sites
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Explore experience ↗◷ 4 hr
Sail from Key West Bight aboard Papa’s Cat, a 48-ft catamaran inspired by Hemingway’s island spirit. Dive vibrant reefs, drift over sug
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Explore experience ↗◷ 2 hr
Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests Leave the crowds behind and experience the magic of a
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Explore experience ↗◷ 24 hr
The 21' Hurricane Sundeck is the perfect blend of comfort, versatility, and performance, making it a top choice for adventurers and fam
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Explore experience ↗◷ 24 hr
The 24' Hurricane Sundeck stands out as the ultimate choice for families and groups looking for comfort and versatility on the water. I
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Explore experience ↗◷ 24 hr
Experience the ultimate adventure aboard our 25' Cobia Center Console with twin engines, designed for power, stability, and comfort. Pe
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Explore experience ↗◷ 96 hr
This private Florida Keys yacht charter combines daytime exploration with an overnight stay aboard a Jeanneau NC 895 Weekender. The pre
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View datesIn Key West, first-time sailors can find the perfect sunset cruise or calm day sail, but one choice makes all the difference.
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