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 -
Island Adventure Snorkel Kayak and Tour
Discover a different side of Key West as you explore a secluded paradise in the Florida Keys backcountry on this Island Adventure.
... Read More4 hours 30 minutesBest RateDetails
116.04Best RateDetails
116.04 -
Key West Classic Day Sail Aboard America 2.0
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0!
... Read More1 hour 30 minutesBest RateDetails
68.80Best RateDetails
68.80 -
Key West Wind & Wine Private Charter
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running.
... Read More2.5 Hours (approx.)Best RateDetails
2,500Best RateDetails
2,500 -
Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak
Set sail aboard our classically-styled schooner as she departs Key West's Historic Seaport for a full day of sailing and exploration through the pristine waters of the Gulf of Mexico.
... Read More6 hoursBest RateDetails
108.95Best RateDetails
108.95 -
Mimosa Day Sail aboard Schooner America 2
Take to the water on the fastest, most elegant sailboat in Key West, Schooner America 2.0.
... Read More1 hour 30 minutesBest RateDetails
68.80Best RateDetails
68.80 -
All-In-One Sail, Kayak, Snorkel aboard 32′ Java Cat
Dolphins, sea turtles or "flyin" rays may cross your path as you enter "The Lake", jewel of the Key West National Wildlife Refuge.
... Read More4 hoursBest RateDetails
123.63Best RateDetails
123.63 -
Reef Snorkel & Sail Adventure – Morning
Join us for a snorkel adventure to the only living coral reef in North America.
... Read More3 hoursBest RateDetails
69Best RateDetails
69 -
Reef Snorkel & Sail Adventure – Afternoon
Join us for a snorkel adventure to the only living coral reef in North America.
... Read More3 hoursBest RateDetails
69Best RateDetails
69 -
Half-Day Cruise with Kayaking and Snorkeling
Don't miss one of the top things to do in Key West—a half-day sailing tour where you can explore the waters of the Florida Keys.
... Read More4 hours 30 minutesBest RateDetails
77.40Best RateDetails
77.40 -
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