Key West Sailing Trips
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
$85Key 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- 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
$120Key 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!
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$450Best RateDetails
$450Reef Snorkel & Sail Adventure – Morning
Join us for a snorkel adventure to the only living coral reef in North America.
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$69Best RateDetails
$69Reef Snorkel & Sail Adventure – Afternoon
Join us for a snorkel adventure to the only living coral reef in North America.
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$69Best RateDetails
$69Half-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
$77.40Key West Sunset Sail Aboard Schooner America 2.0
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner!
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$103.20Best RateDetails
$103.20Key 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
$114.95Schooner 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
$38.95Wild 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
$95.59Group 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
$68All 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
$129Sunset Sip & Sail
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat.
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$52.68Best RateDetails
$52.68