Key West Cruises, Sailing & Water Tours

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

Fish like never before! Our custom build 64' catamaran is perfect for a more stable, relaxing ride. You'll fish for a wide variety of the...

This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters...

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded...

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Tours of Key West three years running. See the...

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef...

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure...

Tours of Key West is the only tour operator in Key West offering sailing excursions on a historic schooner into the remote backcountry of the...

Explore the serene mangrove waterways of Geiger Key on this guided eco-tour. Perfect for all ages and levels of experience. Choose between a single kayak,...