Key West Powerboat Races

Guaranteed to be one of the most thrilling experiences of your life, Key West Powerboat Races get more legendary and powerful every year. The one time of the year where our laidback Key West pace gives way to pulse-pounding speed. Why’d the chicken cross the road? 125-mph Key West Powerboat Races! This opportunity sells out every year, be sure to book early.

Read More
  • Key West Original Watersports Adventure

    Key West Original Watersports Adventure

    Get ready for the thrill of a lifetime with our Do It All Watersports Combo, the ultimate way to experience the best of Key West!...
    Read More

     6 hours  Free Cancellation  Instant Confirmation
    from
    $179.95
    Details
    from
    $179.95
  • Key West Schooner Sunset Sail with Hors D’oeuvres and Full Bar

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

    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...
    Read More

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Details
    Best Rate
    $99.95
  • Key West Dolphin Watch & Snorkel Tour with FREE shuttle to location
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Dolphin Watch & Snorkel Tour with FREE shuttle to location

    Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....
    Read More

     3 hours 30 minutes (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $99
    Details
    Best Rate
    $99
  • Key West Sunset Dinner Cruise
    Likely to Sell Out

    Key West Sunset Dinner Cruise

    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....
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $92.95
    Details
    from
    $92.95
  • Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
    Special Offer

    Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

    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...
    Read More

     2 hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $99
    $89
    Details
    $99
    $89
  • Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

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

    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...
    Read More

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $79.95
    Details
    Best Rate
    $79.95
  • Sunset Sip & Sail
    Likely to Sell Out

    Sunset Sip & Sail

    Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...
    Read More

     2 hours  Free Cancellation
    from
    $72
    Details
    from
    $72
  • Key West Dolphin Watch Sunset Snorkel Cruise
    Likely to Sell Out

    Key West Dolphin Watch Sunset Snorkel Cruise

    The Cool Key West Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    Details
    from
    $69.95
  • Key West Sunset Snorkel Sail
    Likely to Sell Out

    Key West Sunset Snorkel Sail

    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...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    Details
    from
    $69.95
Filter
Language
Currency

Site Settings

Activity name

Currency

Activity name

Sorting, ranking, and search results

Activity name

Cool 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 Cool 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.