Vehicle Rentals Top 10 Key West

Best For Romance

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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 Backcountry Safari
    Likely to Sell Out
    Top10Top 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 (2,487)

    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 Wind & Wine Sunset Sail
    Likely to Sell Out
    Top10Top 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 (1,569)

    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 Private Wind & Wine Charter (for up to 30 guests)
    5.0 (1,569)

    Key West Private Wind & Wine Charter (for up to 30 guests)

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

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $3,499
    Best Rate
    $3,499
  • Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar
    4.8 (3,476)

    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...

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $79.95
    Best Rate
    $79.95
  • Key West Schooner Sunset Sail with Hors D’oeuvres and Full Bar
    4.9 (1,596)

    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...

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Best Rate
    $99.95
  • Key West Sunset Dinner Cruise
    Likely to Sell Out
    Likely to Sell Out
    4.4 (1,682)

    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....

     2 hours  Free Cancellation  Instant Confirmation
    from
    $92.95
    from
    $92.95
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