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Top 10 Key West Tours in 2025

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Key West Tours

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The Cool Key West Top 10 Key West is the original best of Key West list. These tours and activities are hand-selected and fun-tested to provide the most excitement for the best prices on the island. When you book a Top 10 Key West tour you can be sure you are choosing from the very Best Things To Do in Key West. The only hard part is choosing which Top 10 Tour to go out on!

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  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out
    1Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    5.0 (1,561)

    Key West Wind & Wine Sunset Sail

    Wind & Wine has been the #1 rated sunset sail on Cool Key West for over a decade. In our opinion, this is the best

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    $109
    $99
  • Key West Original Island Jet Ski Tour
    Likely to Sell Out
    2Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (2,889)

    Key West Original Island Jet Ski Tour

    Enjoy exciting high-speed watersports fun with the best Key West jet ski tour – the Key West Original Island Jet Ski Tour, a guided 28-mile

     1 hour 30 minutes (approx.)  Free Cancellation  Instant Confirmation
    $159
    $99
    $159
    $99
  • Key West Dolphin Watch & Snorkel Tour with FREE shuttle to location
    3Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    4.9 (24)

    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.

     3 hours 30 minutes (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $99
    Best Rate
    $99
  • Key West Split Fishing Charter
    Likely to Sell Out
    4Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.8 (493)

    Key West Split Fishing Charter

    Cool Key West presents the Key West Split Fishing Charter: the most cost-effective and convenient way to get offshore and enjoy some Key West sportfishing.

     4 or 6 hours (approx.)  Free Cancellation
    $350
    $200
    $350
    $200
  • Key West 6 Seater EZGO Golf Cart Rental
    5Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    4.9 (1,080)

    Key West 6 Seater EZGO Golf Cart Rental

    Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express

     3 hours and up  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $170
    Best Rate
    $170
  • Key West Backcountry Safari
    Likely to Sell Out
    6Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (2,484)

    Key West Backcountry Safari

    Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness.

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $120
    $99
    $120
    $99
  • Key West Dive in a Day Scuba Resort Course
    Likely to Sell Out
    7Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (138)

    Key West Dive in a Day Scuba Resort Course

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

     9 hours (approx.)  Free Cancellation  Instant Confirmation
    $269
    $229
    $269
    $229
  • Key West 4 Seater Electric Car Rental
    Likely to Sell Out
    8Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (901)

    Key West 4 Seater Electric Car Rental

    Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car

     3 hours and up  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $90
    Best Rate
    $90
  • Key West Private Deep Sea Fishing Charter (up to 41 passengers)
    Likely to Sell Out
    9Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (18)

    Key West Private Deep Sea Fishing Charter (up to 41 passengers)

    Cool Key West brings you the ultimate Private Deep Sea Fishing Charter experience with a classic 63-foot sportfishing boat that can show 41 day-trip guests

     4-12 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $1,700
    Best Rate
    $1,700
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out
    10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (2,484)

    Key West Sail, Snorkel, Kayak with Sunset Option

    Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge.

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $99
    $90
    $99
    $90
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Cool Things To Do in Key West

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We guarantee the lowest price on all the activities available to book on our site. We'll refund the difference if you find the exact activity cheaper online until 48 hours before your activity 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.
  • Cool Key West promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same activity, 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 Cool 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 activity into one or more parts sold separately.
  • Cool 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 Cool Key West.

Sorting, ranking, and search results

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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.

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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.

Miscellaneous

  • 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.