62 experiences to discover
Explore the best cruises & sailing tours tours and activities in Key West. Our unbiased ratings help you find the perfect experiences for your trip.
From $80
Sail into a stunning Key West sunset
Two marine heads
From $114
Explore the scenic waters of Marathon
Soda/Pop
From $105
Sail across the serene Wai Kai Lagoon
1-hour Hobie Wave Cat rental
From $95
Sail on Key West's iconic tall ship
Coolers of ice with cups and bottled water
From $395
Sail the scenic Key West harbor
Bottled water
$140-$151
Cruise through mangrove channels
Experience breathtaking Key West sunsets
Catamaran cruise
From $403
Set sail for a unique tiki adventure
Licensed Captain
From $110
Savor a Key West sunset on a classic schooner
Homemade sangria, wine, beer, liquor, soft drinks, and filtered water
From $109
Sail into the sunset on a classic schooner
From $120
Sail a tall ship to Key West's backcountry
Sail on a tall ship
$600-$661
Cruise through scenic mangrove trails
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