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Key West Sailing Trips

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Key West Tours

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  • Key West Wind & Wine Private Charter

    140

    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
    $3,000
    Details
    Best Rate
    $3,000
    Details
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Wind & Wine Sunset Sail

    87

    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
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Backcountry Safari

    256

    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
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sail, Snorkel, Kayak with Sunset Option

    256

    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
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

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

    171

    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
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Harbor Cruise

    58

    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
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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):