Valentine’s in Key West!

Have an adventure this Valentine’s Day in Key West with the one you love. Join Inside Key West for a perfect sunset sail, a romantic day sailing, snorkeling, and kayaking, or go all out with jet ski tour around the island.

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  • Key West Deep Sea Fishing Charter
    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.

    Key West Deep Sea Fishing Charter

    Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter...
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     4, 6 or 8 hours (approx.)  Free Cancellation
    $1,000
    $900
    Details
    $1,000
    $900
  • Key West Split Fishing Charter
    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.

    Key West Split Fishing Charter

    On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...
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     4 or 6 hours (approx.)  Free Cancellation
    $350
    $200
    Details
    $350
    $200
  • 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.

    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...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    Details
    $109
    $99
  • Key West Sail, Snorkel, Kayak with Sunset Option
    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.

    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....
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     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $99
    $90
    Details
    $99
    $90
  • Key West Sunset Harbor Cruise
    Special Offer

    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...
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     2 hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $99
    $89
    Details
    $99
    $89
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Inside 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 Inside 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.