Key West Sailing Trips

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Featured

Key West Sunset Harbor Cruise
30
Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...
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2 Hours (approx.) Hotel pickup offered Instant Confirmation
~~$75~~
$69
Details
~~$75~~
$69
Details
Key West Wind & Wine Sunset Sail
70
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running....
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2 Hours (approx.) Instant Confirmation
~~$95~~
$90
Details
~~$95~~
$90
Details
Key West Backcountry Safari
192
Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....
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6.5 or 4.5 hours (approx.) Instant Confirmation
~~$120~~
$115
Details
~~$120~~
$115
Details
Key West Sail, Snorkel, Kayak with Sunset Option
192
Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....
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4.5 or 6.5 hours (approx.) Instant Confirmation
~~$99~~
$90
Details
~~$99~~
$90
Details
Key West Morning Mimosa Private Charter
3
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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2 Hours (approx.) Hotel pickup offered Instant Confirmation
~~$1,850~~
$1,700
Details
~~$1,850~~
$1,700
Details
Key West Wind & Wine Private Charter
46
The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on...
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2.5 Hours (approx.)
Best Rate
$2,500
Details
Best Rate
$2,500
Details
Key West Full-Day Island T’ing Eco-Tour: Sail, Snorkel and Kayak Adventure
122
Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...
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6 hours (approx.) Instant Confirmation
~~$124.95~~
$119.95
Details
~~$124.95~~
$119.95
Details

Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Key West Sailing Trips?

A: According to verified reviews on Jet Skis Key West and TripAdvisor, the best Key West Sailing Trips are:

Q: What Key West Sailing Trips are taking additional safety precautions?

A: The following activities in Key West experiences are providing additional COVID-19 safety measures (to read the specific policies please click the activity name and read the "Keeping you safe during COVID-19" section located underneath the booking calendar):

Key West Sailing Trips

Key West Tours

Key West Sunset Harbor Cruise

Key West Wind & Wine Sunset Sail

Key West Backcountry Safari

Key West Sail, Snorkel, Kayak with Sunset Option

Key West Morning Mimosa Private Charter

Key West Wind & Wine Private Charter

Key West Full-Day Island T’ing Eco-Tour: Sail, Snorkel and Kayak Adventure

Frequently Asked Questions

Q: What are the best options for Key West Sailing Trips?

Q: What Key West Sailing Trips are taking additional safety precautions?