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Key West Sailing

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Key West Tours

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  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Sail, Snorkel, Kayak with Sunset Option

    2,259

    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.)  Free Cancellation  Instant Confirmation
    $99
    $90
    Details
    $99
    $90
    Details
  • Key West Backcountry Safari
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Backcountry Safari

    2,259

    Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....
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     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $120
    $99
    Details
    $120
    $99
    Details
  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Wind & Wine Sunset Sail

    1,407

    Wind & Wine has been the #1 rated sunset sail on Inside Key West for over a decade. In our opinion, this is the best...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    Details
    $109
    $99
    Details
  • Key West Sunset Harbor Cruise
    Special Offer

    Key West Sunset Harbor Cruise

    120

    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  Free Cancellation  Instant Confirmation
    $99
    $89
    Details
    $99
    $89
    Details
  • Key West Wind & Wine Private Charter

    Key West Wind & Wine Private Charter

    1,407

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Inside Key West three years running. See the sunset...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $3,499
    Details
    Best Rate
    $3,499
    Details
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Travelers like you also enjoyed...

  • Key West Original Island Jet Ski Tour
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Original Island Jet Ski Tour

    2,638

    On our Key West Island Jet Ski Tours you jump on one of our Yamaha Waverunners and cruise around the island on a 26 mile,...
    Read More

     1 hour 30 minutes (approx.)  Free Cancellation  Instant Confirmation
    $159
    $99
    Details
    $159
    $99
    Details
  • Miami to Key West Day Trip with Snorkeling
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Miami to Key West Day Trip with Snorkeling

    2,831

    Take a luxury coach tour from Miami to Key West then cruise out on the emerald waters to enjoy a Key West snorkeling trip on...
    Read More

     6 hours in Key West (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $141
    $119
    Details
    $141
    $119
    Details
  • Key West Deep Sea Fishing Charter
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Deep Sea Fishing Charter

    251

    Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter...
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     4, 6 or 8 hours (approx.)  Free Cancellation
    $1,000
    $900
    Details
    $1,000
    $900
    Details
  • Key West Split Fishing Charter
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Split Fishing Charter

    471

    On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...
    Read More

     4 or 6 hours (approx.)  Free Cancellation
    $350
    $200
    Details
    $350
    $200
    Details
  • Key West Dive in a Day Scuba Resort Course
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Dive in a Day Scuba Resort Course

    127

    The is the absolute best way for a person to experience diving. Great for those who want to try scuba diving in Key West....
    Read More

     9 hours (approx.)  Free Cancellation  Instant Confirmation
    $269
    $229
    Details
    $269
    $229
    Details
  • Key West Flats Fishing Charter
    Likely to Sell Out

    Key West Flats Fishing Charter

    60

    Take your own private boat and personal guide to hunt Bonefish, Permit, Sharks and other game fish in the crystal-clear waters of the Key West...
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     4, 6 or 8 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $580
    Details
    Best Rate
    $580
    Details
  • Key West Morning 2-Tank SCUBA Dive

    Key West Morning 2-Tank SCUBA Dive

    85

    The morning two tank Key West Dive Trips are great because this includes a double dive in a Vandenberg wreck dive....
    Read More

     4 hours 30 minutes (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $99
    Details
    Best Rate
    $99
    Details
  • Key West Party Boat Fishing Charter

    Key West Party Boat Fishing Charter

    137

    Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West...
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     6 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $69.69
    Details
    Best Rate
    $69.69
    Details
  • Key West Dolphin Watch & Snorkel
    Top10Top 10 Tour Ranked using exclusive Inside Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Dolphin Watch & Snorkel

    23

    Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....
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     3 hours 30 minutes (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $99
    Details
    Best Rate
    $99
    Details
  • Key West Snuba® (No Dive Certification Required)

    Key West Snuba® (No Dive Certification Required)

    452

    If you want to go beyond snorkeling and experience the world's underwater beauty in the safest and easiest way possible, try Snuba®!...
    Read More

     3 hours  Instant Confirmation
    from
    $145
    Details
    from
    $145
    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?

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

Q: What are the best kid-friendly options for Key West Sailing Things To Do?

A: According to verified reviews on Inside Key West and TripAdvisor, the best kid-friendly Key West Sailing are:

View all kid-friendly Things To Do →

Q: Which Key West Sailing have Instant Confirmation?

A: Key West Sailing with Instant Confirmation include:

View all Things To Do with Instant Confirmation →

Q: Which Key West Sailing have Free Cancellation?

A: Key West Sailing with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Things To Do with Free Cancellation →

Q: I need a ride! Which Key West Sailing include Hotel Pickup?

A: No problem. These Key West Sailing include Hotel Pickup:

View all Things To Do with Hotel Pickup →

Things To Do in Key West

Lowest Price Guarantee

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

We guarantee the lowest price on all the things to do available to book on our site. We'll refund the difference if you find the exact tour cheaper online until 48 hours before your tour starts.

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The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Inside Key West promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Inside Key West and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased tour into one or more parts sold separately.
  • Inside Key West reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Inside Key West.

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Inside Key West wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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