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Key West Cruises, Sailing & Water Tours

  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out
    Likely to Sell Out

    Key West Wind & Wine Sunset Sail

    4.95 (1,548)

    Wind & Wine has been the #1 rated sunset sail on Tours of Key West for over a decade. In our opinion, this is the...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    Details
    $109
    $99
  • Miami to Key West Day Trip with Glass Bottom Boat Cruise
    Likely to Sell Out
    Likely to Sell Out

    Miami to Key West Day Trip with Glass Bottom Boat Cruise

    4.60 (3,030)

    Sightsee along the famous Overseas Highway then take a Key West Glass-Bottom Boat Cruise when you tour Key West on this great Miami to Key...
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     6 hours in Key West (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $159
    $119
    Details
    $159
    $119
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out
    Likely to Sell Out

    Key West Sail, Snorkel, Kayak with Sunset Option

    4.93 (2,472)

    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
  • Key West Backcountry Safari
    Likely to Sell Out
    Likely to Sell Out

    Key West Backcountry Safari

    4.93 (2,472)

    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
  • Key West Sunset Dinner Cruise
    Likely to Sell Out
    Likely to Sell Out

    Key West Sunset Dinner Cruise

    4.41 (1,668)

    Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $92.95
    Details
    from
    $92.95
  • Key West Mangrove Kayak Eco Tour

    Key West Mangrove Kayak Eco Tour

    4.91 (2,162)

    Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $70
    Details
    from
    $70
  • Sunset Sip & Sail
    Likely to Sell Out
    Likely to Sell Out

    Sunset Sip & Sail

    4.66 (322)

    Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...
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     2 hours  Free Cancellation
    from
    $72
    Details
    from
    $72
  • Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

    Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

    4.80 (3,443)

    Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $79.95
    Details
    Best Rate
    $79.95
  • Key West Sunset Harbor Cruise
    Special Offer
    Special Offer

    Key West Sunset Harbor Cruise

    4.91 (123)

    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
  • Key West Dolphin Watch Sunset Snorkel Cruise
    Likely to Sell Out
    Likely to Sell Out

    Key West Dolphin Watch Sunset Snorkel Cruise

    4.67 (307)

    The Tours of Key West Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    Details
    from
    $69.95
  • Schooner Appledore Key West Premium Sunset Sail with Hors D’oeuvres and Full Bar

    Schooner Appledore Key West Premium Sunset Sail with Hors D’oeuvres and Full Bar

    4.94 (1,584)

    Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Details
    Best Rate
    $99.95
  • Key West Sunset Snorkel Sail
    Likely to Sell Out
    Likely to Sell Out

    Key West Sunset Snorkel Sail

    4.79 (147)

    Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    Details
    from
    $69.95
  • Key West Sunset Sail Aboard Schooner America 2.0
    Likely to Sell Out
    Likely to Sell Out

    Key West Sunset Sail Aboard Schooner America 2.0

    4.94 (1,584)

    Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $116.10
    Details
    from
    $116.10
  • Key West Shark and Wildlife Catamaran Tour
    Likely to Sell Out
    Likely to Sell Out

    Key West Shark and Wildlife Catamaran Tour

    4.97 (2,803)

    This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $99
    Details
    from
    $99
  • Key West Dolphin Watch & Snorkel

    Key West Dolphin Watch & Snorkel

    4.88 (24)

    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
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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 Cruises, Sailing & Water Tours?

A: According to verified reviews on Tours of Key West and TripAdvisor, the best Key West Cruises, Sailing & Water Tours are:

Q: What are the best kid-friendly options for Key West Cruises, Sailing & Water Tours Tours?

A: According to verified reviews on Tours of Key West and TripAdvisor, the best kid-friendly Key West Cruises, Sailing & Water Tours are:

View all kid-friendly Tours

Q: Which Key West Cruises, Sailing & Water Tours have Instant Confirmation?

A: Key West Cruises, Sailing & Water Tours with Instant Confirmation include:

View all Tours with Instant Confirmation

Q: Which Key West Cruises, Sailing & Water Tours have Free Cancellation?

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

View all Tours with Free Cancellation

Q: I need a ride! Which Key West Cruises, Sailing & Water Tours include Hotel Pickup?

A: No problem. These Key West Cruises, Sailing & Water Tours include Hotel Pickup:

View all Tours with Hotel Pickup

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Tours of 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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The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Cool Rewards Terms & Conditions

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Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

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  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
  • We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.