Key West Cruises & Sailing Tours - Page 3

62 experiences to discover

Day & Sunset Cruises Dinner Cruises Sailing Trips

Explore the best cruises & sailing tours tours and activities in Key West. Our unbiased ratings help you find the perfect experiences for your trip.

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4.54

Key West Catamaran Champagne Sunset Sail 1.5 hr

From $80

1 provider live

Sail into a stunning Key West sunset

Two marine heads

4.54

Marathon Sandbar Cruise & Sightseeing Adventure

From $114

1 provider live

Explore the scenic waters of Marathon

Soda/Pop

4.53

Key West Hobie Wave Cat Rental

From $105

1 provider live

Sail across the serene Wai Kai Lagoon

1-hour Hobie Wave Cat rental

4.52

Key West Sunset Sail Cruise

From $95

1 provider live

Sail on Key West's iconic tall ship

Coolers of ice with cups and bottled water

4.52

Key West Harbor Sailing Charter

From $395

1 provider live

Sail the scenic Key West harbor

Bottled water

4.52

Key West Sandbar Cruise with Lunch

$140-$151

2 providers combined

Cruise through mangrove channels

Soda/Pop

4.5

Key West Sunset Sail with Live Music

From $80

2 providers combined

Experience breathtaking Key West sunsets

Catamaran cruise

4.5

Key West Tiki Boat Party & Mini Sandbar 2 hr

From $403

1 provider live

Set sail for a unique tiki adventure

Licensed Captain

4.48

Key West Schooner Appledore Star Sunset Sail

From $110

1 provider live

Savor a Key West sunset on a classic schooner

Homemade sangria, wine, beer, liquor, soft drinks, and filtered water

4.46

Key West Schooner Sunset Sail with Open Bar

From $109

1 provider live

Sail into the sunset on a classic schooner

Soda/Pop

4.45

Key West National Wildlife Refuge Full Day Tour

From $120

1 provider live

Sail a tall ship to Key West's backcountry

Sail on a tall ship

4.45

Key West Sandbar Boat Tour and Swim

$600-$661

2 providers combined

Cruise through scenic mangrove trails

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