Key West Cruises & Sailing Tours

9 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:

4.66

Key West Schooner Sunset Sail with Drinks

From $116

Sail into a breathtaking Key West sunset

Sailboat tour

4.58

Key West Sunset Sail with Wine and Hors d'oeuvres

From $134

Sail into the vibrant Key West sunset

Premium wine and cold beer

4.58

Key West Sandbar Cruise with Lunch and Open Bar

$140-$151

Cruise on a modern vessel with cushioned seating

Paddle boards, lily pad mat, personal floats, water toys

4.56

Key West Schooner Sail with Drinks 1.5 hr

$65-$73

Sail aboard the elegant Schooner America 2.0

1.5-hour coastal sailing tour

4.55

Key West Sandbar Safari Tiki Cruise

$99-$119

Cruise on a unique tiki boat

Soda/Pop

4.55

Key West Sandbar Cruise with Lunch and Open Bar

$129-$151

Travel on a new vessel with cushioned seating

Paddle boards, Lily Pad Mat, Personal Floats, Water Toys

4.53

Key West Sandbar & Sunset Cruise with Happy Hour

From $150

Savor unlimited drinks at the sandbar

Lily pad

3.55

Key West Dolphin Watching and Snorkeling Sunset Cruise

$70-$71

Marvel at playful dolphins in their natural habitat

Soda/Pop

2.24

Key West Sunset Dinner Cruise with Live Music

From $93

Marvel at the sunset over the Gulf of Mexico

Buffet dinner