Key West Cruises & Sailing Tours - Page 4

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:

4.46

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

4.43

Key West Dolphin Watch and Sunset Sail

From $117

2 providers combined

Watch dolphins in their natural habitat

Fresh organic snacks from a local cafe

4.43

Key West Schooner Sunset Sail with Open Bar

From $109

1 provider live

Sail into the sunset on a classic schooner

Soda/Pop

4.4

Key West Schooner Day Sail with Cocktails

From $49

1 provider live

Sail with a warm tropical breeze

Signature Bloody Mary or Dark & Stormy cocktails

4.4

Key West Sunset Sail Private Charter 2 Hr

From $695

1 provider live

Sail into the sunset on a private charter

Light refreshments

4.4

Key West Dolphin Watch Sunset Sail

From $90

1 provider live

Sail into a stunning sunset

Two marine heads

4.39

Key West Tiki Bar Boat Sandbar Tour

From $565

1 provider live

Explore turquoise waters on a tiki bar boat

Bottled water

4.37

Key West Private Sunset Cruise on Tiki Bar Boat

From $457

1 provider live

Cruise Key West harbor at sunset

USCG Certified Captain/Guide

4.31

Key West Historic Schooner Sunset Cruise

From $109

1 provider live

Sail into a stunning Key West sunset

Soda/Pop

4.26

Key West Tiki Boat Sunset Cruise 2 hr

From $457

1 provider live

Ride on a custom tiki bar boat

Captain

4.26

Key West Cocktail Cruise at Sunset

From $65

1 provider live

Savor unlimited craft cocktails

Unlimited drinks (open bar)

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