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
$450Wild 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
$52.68Small-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.
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$91.38Best RateDetails
$91.38Key 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
$52.68Famous 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
$59Private 90 Minute Customized Sailing Charter
Live the high life on this private chartered day sail in Key West.
... Read More1 hour 30 minutesBest RateDetails
$294.99Best RateDetails
$294.99Island 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
$116.04Key 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