Key West Sailing Trips
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Key West Sail, Snorkel, Kayak with Sunset Option
Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge.
... Read More4.5 Hours (approx.)Best RateDetails
80Best RateDetails
80 -
Key West Wind & Wine Sunset Sail
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.
... Read More2 Hours (approx.)Best RateDetails
85Best RateDetails
85 -
Best RateDetails
75 -
Key West Backcountry Safari
Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness.
... Read More6.5 Hours (approx.)Best RateDetails
120Best RateDetails
120 -
Key West Morning Mimosa Private Charter
This exclusive experience is for 1 to 40 persons as a private charter and includes unlimited pastries, juices, coffee and mimosas for your group!
... Read More2 Hours (approx.)Best RateDetails
450Best RateDetails
450 -
Key West Sunset Sail Aboard Schooner America 2.0
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner!
... Read More2 hoursBest RateDetails
103.20Best RateDetails
103.20 -
Key West Full-Day Island T’ing Eco-Tour: Sail, Snorkel and Kayak Adventure
Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and snorkeling the perfect way to spend a fun day in the sun.
... Read More6 hoursBest RateDetails
114.95Best RateDetails
114.95 -
Schooner Appledore Key West Day and Sunset Cruises with Full Bar
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner.
... Read More2 hoursBest RateDetails
38.95Best RateDetails
38.95 -
Wild Dolphin Sail & Shallow-water Snorkel
Spend a beautiful Florida day out in the clear, blue waters on a snorkeling and dolphin-watching sailing excursion.
... Read More4 hoursBest RateDetails
95.59Best RateDetails
95.59 -
Group Sunset Cruise
The Solé Watersports Sunset Cruise at Hawks Cay Resort is the only Sunset Cruise in the Duck Key area.
... Read More1 hour 30 minutesBest RateDetails
68Best RateDetails
68 -
All Inclusive Water Adventure Excursion in Key West
This full day excursion from Key West includes all the fun things to do in the ocean - kayaking, snorkeling and sailing!
... Read More6 hours 30 minutesBest RateDetails
129Best RateDetails
129 -
Sunset Sip & Sail
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat.
... Read More2 hoursBest RateDetails
52.68Best RateDetails
52.68 -
Small-Group Sunset Sail with Wine
Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres.
... Read More2 hoursBest RateDetails
91.38Best RateDetails
91.38 -
Key West Sunset Snorkel Sail
3 Hour Sunset Snorkel Sail See the Living Coral Reef watch the World Famous Key West Sunset Have a cool beverage.
... Read More3 hoursBest RateDetails
52.68Best RateDetails
52.68 -
Famous Key West Sunset Sail
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise.
... Read More1 hour 30 minutesBest RateDetails
59Best RateDetails
59