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.

Sort by:

4.21

Key West Sandbar Adventure & Sunset Cruise

$127-$137

2 providers combined

Savor unlimited drinks at the sandbar

Unlimited draft beer, mimosas, wine, and champagne

4.19

Key West Sandbar Tiki Cruise 3.5 hr

From $139

2 providers combined

Cruise through crystal-clear waters

Tiki Cruise

4.15

Key West Tiki Bar Sunset Cruise BYOB 2 hr

From $81

1 provider live

Toast the sunset with your favorite drink

Life vests

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

3.93

Key West Dolphin Catamaran Sail

$59-$60

2 providers combined

Sail on a 60' catamaran

Roundtrip catamaran ride

3.92

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

3.84

Key West Sunset Sail with Beverages

From $79

1 provider live

Sail into the sunset on a beautiful sailboat

Non-alcoholic beverages

3.8

Key West Sushi Sunset Cruise

From $75

1 provider live

Savor sushi and charcuterie

Soda/Pop

3.45

Key West Dolphin Watching and Snorkeling Cruise

$70-$72

2 providers combined

Marvel at playful dolphins in their natural habitat

Soda/Pop

3.18

Key West Sunset Cruise with Open Bar and Music

$72-$80

2 providers combined

Watch the sun set over the horizon

Food and drinks

3.14

Key West Sunset Sail with Live Music

From $80

2 providers combined

Experience breathtaking Key West sunsets

Catamaran cruise

2.8

Key West Sunset Sail and Dolphin Watching

From $89

2 providers combined

Sail into the sunset on a luxury catamaran

Soda/Pop