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Best For Romance

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Key West Tours

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Couples can have a great time exploring the natural nooks and coves of the mangrove islands by kayak or snorkeling hand-in-hand over the colorful living reef. Key West is for lovers, and nothing makes for Romance like an afternoon playing in the blue water followed by a champagne toast as you sail into the sunset.

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  • Key West Sunset Harbor Cruise
    Special Offer
    Special Offer
    4.9 (124)

    Key West Sunset Harbor Cruise

    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...

     2 hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $99
    $89
    $99
    $89
  • 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.
    Likely to Sell Out
    5.0 (1,564)

    Key West Wind & Wine Sunset Sail

    Wind & Wine has been the #1 rated sunset sail on Inside 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 Wind & Wine Private Charter
    5.0 (1,564)

    Key West Wind & Wine Private Charter

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Inside Key West three years running. See the sunset...

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $3,499
    Best Rate
    $3,499
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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).
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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.

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  • 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.
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  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
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  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.