(855) 274-1023 Key West Questions? Call Us Now!

Key West Sailing Trips

  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out

    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....
    Read More

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $99
    $90
    Details
    $99
    $90
    Details
  • Key West Backcountry Safari
    Likely to Sell Out

    Key West Backcountry Safari

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

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $120
    $99
    Details
    $120
    $99
    Details
  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out

    Key West Wind & Wine Sunset Sail

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

     2 hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    Details
    $109
    $99
    Details
  • 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
    $79.95
    Details
    from
    $79.95
    Details
  • 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...
    Read More

     2 hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $99
    $89
    Details
    $99
    $89
    Details
  • 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
    $56.95
    Details
    from
    $56.95
    Details
  • Key West Sunset Sail Aboard Schooner America 2.0
    Likely to Sell Out

    Key West Sunset Sail Aboard Schooner America 2.0

    Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $116.10
    Details
    from
    $116.10
    Details
  • Key West Full-Day Island T’ing Eco-Tour: Sail, Snorkel and Kayak Adventure
    Special Offer

    Key West Full-Day Island T’ing Eco-Tour: Sail, Snorkel and Kayak Adventure

    Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...
    Read More

     6 hours (approx.)  Free Cancellation  Instant Confirmation
    $124.95
    $119.95
    Details
    $124.95
    $119.95
    Details
  • Famous Key West Sunset Sail
    Likely to Sell Out

    Famous Key West Sunset Sail

    Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...
    Read More

     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Reef Snorkel & Sail Adventure – Afternoon
    Likely to Sell Out

    Reef Snorkel & Sail Adventure – Afternoon

    Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

    Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

    Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...
    Read More

     5 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $109.95
    Details
    Best Rate
    $109.95
    Details
  • Reef Snorkel & Sail Adventure – Morning
    Likely to Sell Out

    Reef Snorkel & Sail Adventure – Morning

    Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Wild Dolphin Sail & Shallow-water Snorkel
    Likely to Sell Out

    Wild Dolphin Sail & Shallow-water Snorkel

    All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo...
    Read More

     4 hours  Instant Confirmation
    from
    $108.91
    Details
    from
    $108.91
    Details
  • Small-Group Sunset Sail with Wine
    Likely to Sell Out

    Small-Group Sunset Sail with Wine

    The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $128.89
    Details
    from
    $128.89
    Details
  • Half-Day Cruise with Kayaking and Snorkeling
    Likely to Sell Out

    Half-Day Cruise with Kayaking and Snorkeling

    This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters...
    Read More

     4 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $117.07
    Details
    from
    $117.07
    Details
Filter

Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Key West Sailing Trips?

A: According to verified reviews on Tours of Key West and TripAdvisor, the best Key West Sailing Trips are:

Q: What are the best kid-friendly options for Key West Sailing Trips Tours?

A: According to verified reviews on Tours of Key West and TripAdvisor, the best kid-friendly Key West Sailing Trips are:

View all kid-friendly Tours

Q: Which Key West Sailing Trips have Instant Confirmation?

A: Key West Sailing Trips with Instant Confirmation include:

View all Tours with Instant Confirmation

Q: Which Key West Sailing Trips have Free Cancellation?

A: Key West Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation

Q: I need a ride! Which Key West Sailing Trips include Hotel Pickup?

A: No problem. These Key West Sailing Trips include Hotel Pickup:

View all Tours with Hotel Pickup

Sorting, ranking, and search results

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Tours of 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 Tours of 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.