Key West Cruises & Sailing Tours - Page 5

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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4.24

Key West Tiki Boat Sunset Cruise 2 hr

From $457

1 provider live

Ride on a custom tiki bar boat

Captain

4.23

Key West Sandbar Tiki Cruise 3.5 hr

From $139

2 providers combined

Cruise through crystal-clear waters

Tiki Cruise

4.19

Key West Private Sunset Cruise on Tiki Bar Boat

From $457

1 provider live

Cruise Key West harbor at sunset

USCG Certified Captain/Guide

4.19

Key West Schooner Day Sail with Drinks 1.5 hr

From $79

2 providers combined

Sail the elegant Schooner America 2.0

1.5-hour coastal sailing tour

4.1

Key West Sunset Sail with Beverages

From $79

1 provider live

Sail into the sunset on a beautiful sailboat

Non-alcoholic beverages

4.06

Key West Sunset Cruise

$400-$450

2 providers combined

Experience a private boat tour

Cooler full of ice and bottled water

4.06

Key West Sunset Sail with Champagne and Cheese

From $109

1 provider live

Sail on Key West's beautiful waters

Bottomless Domain Chandon Brut Classic Champagne

3.98

Key West Schooner Sunset Sail

From $123

2 providers combined

Feel the wind as you sail into the sunset

2-hour sailing experience aboard America 2.0

3.96

Key West Dolphin Catamaran Sail

$59-$60

2 providers combined

Sail on a 60' catamaran

Roundtrip catamaran ride

3.84

Key West Sushi Sunset Cruise

From $75

1 provider live

Savor sushi and charcuterie

Soda/Pop

3.53

Key West Sunset Cruise with Open Bar and Music

$72-$80

2 providers combined

Watch the sun set over the horizon

Food and drinks

2.9

Key West Dolphin Watching and Snorkeling Cruise

$70-$72

2 providers combined

Marvel at playful dolphins in their natural habitat

Soda/Pop