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Key West Cruises, Sailing & Water Tours

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Key West Tours

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

    Key West Wind & Wine Sunset Sail

    1,467

    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
    Details
  • Miami to Key West Day Trip with Glass Bottom Boat Cruise
    Likely to Sell Out

    Miami to Key West Day Trip with Glass Bottom Boat Cruise

    2,918

    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
    Details
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out

    Key West Sail, Snorkel, Kayak with Sunset Option

    2,383

    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

    Key West Backcountry Safari

    2,383

    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 Sunset Dinner Cruise
    Likely to Sell Out

    Key West Sunset Dinner Cruise

    1,557

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

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

    3,269

    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
    Details
  • Sunset Sip & Sail
    Likely to Sell Out

    Sunset Sip & Sail

    289

    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
    Details
  • Key West Mangrove Kayak Eco Tour

    Key West Mangrove Kayak Eco Tour

    2,058

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

    Key West Dolphin Watch Sunset Snorkel Cruise

    275

    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
    Details
  • Key West Sunset Harbor Cruise
    Special Offer

    Key West Sunset Harbor Cruise

    121

    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
  • 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

    1,529

    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
    Details
  • Key West Sunset Snorkel Sail
    Likely to Sell Out

    Key West Sunset Snorkel Sail

    137

    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
    Details
  • Key West Sunset Sail Aboard Schooner America 2.0
    Likely to Sell Out

    Key West Sunset Sail Aboard Schooner America 2.0

    1,529

    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
    Details
  • Key West Dolphin Watch & Snorkel

    Key West Dolphin Watch & Snorkel

    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
    Details
  • Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

    Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

    215

    Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...
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     5 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $109.95
    Details
    Best Rate
    $109.95
    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 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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We guarantee the lowest price on all the tours 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 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.
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  • 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 Tours of 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.
  • Tours of 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 Tours of Key West.

Sorting, ranking, and search results

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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.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Tours of Key West over a 12-month period.

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.

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