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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
Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the
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Explore experience ↗◷ 1 hr
This 1-hour boat ride/loop starts at the Spanish Harbor Bridge and goes up to the Bahia Honda Bridge and the Seven Mile Bridge. We’ll c
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Explore experience ↗◷ 5 hr
Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West as so many locals do, visiting littl
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Explore experience ↗◷ 3 hr
Dolphins are widespread in the Florida waters especially Key West as they prefer the warm waters of the tropical ocean. As we visit the
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Explore experience ↗◷ 4 hr
Experience a classic Florida Keys sandbar adventure on a comfortable 53’ catamaran. Cruise through Boot Key Harbor and past scenic land
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Explore experience ↗◷ 4 hr
Welcome to Key West Boat & Jet Ski Adventures! Explore Key West's Backcountry Aboard Our Brand-New Manitou Cruise with Swim Deck Set ou
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Explore experience ↗◷ 1 hr 30 min
Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite b
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Explore experience ↗◷ 1 hr 30 min
Imagine gliding over gentle waves aboard the Lazy Lady, a 53-foot, one of a kind tiki boat. Soak in the vibrant colors of an iconic Key
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Explore experience ↗◷ 2 hr
Set Sail for Tiki Revelry in Key West's Historic Seaplane Basin! Cruise to Key West's unique Seaplane Basin. In the early 1900s, this s
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Explore experience ↗◷ 1 hr 30 min
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favo
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Explore experience ↗◷ 2 hr
Experience a relaxing start to your day on a spacious 53’ luxury catamaran as you cruise through the clear waters surrounding Marathon.
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Explore experience ↗◷ 2 hr
Key West is famous for stunning sunsets, and this dinner cruise offers the perfect way to enjoy them. Savor breathtaking views as the s
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View datesHit the Overseas Highway for Florida Keys stops that promise snorkeling, sunsets, and surprises, but a few hidden highlights might completely change your route.
In Key West, first-time sailors can find the perfect sunset cruise or calm day sail, but one choice makes all the difference.
Get the edge on Key West lobster season—dates, limits, and must-know Florida spiny lobster rules before one small mistake costs your catch.
