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

Key West Sailing Trips

Sailing Trips
Sailing Trips
Boat Tours
Boat Tours
Catamaran Cruises
Catamaran Cruises
Day Cruises
Day Cruises
Dinner Cruises
Dolphin & Whale Watching
Dolphin & Whale Watching
Lunch Cruises
Lunch Cruises
Sunset Cruises
Sunset Cruises
Water Tours
Water Tours
Air, Helicopter & Balloon Tours
Airplane Tours
Boat Rentals
Boat Tours
Bus Tours
Bus Tours
City Tours
City Tours
Classes & Workshops
Classes & Workshops
Cruises, Sailing & Water Tours
Cruises, Sailing & Water Tours
Cultural & Theme Tours
Cultural & Theme Tours
Day Trips
Day Trips & Excursions
Day Trips & Excursions
Deep Sea Fishing
Deep Sea Fishing
Dolphin Tours
Dolphin Tours
Electric Car Rentals
Electric Car Rentals
Fishing
Fishing
Flats Fishing
Flats Fishing
Food, Wine & Nightlife
Food, Wine & Nightlife
Golf Cart Rentals
Golf Cart Rentals
Hop-on Hop-off Tours
Hop-on Hop-off Tours
Jet Ski Tours
Jet Ski Tours
Kayaking
Kid Friendly
Kid Friendly
Light Tackle Fishing
Light Tackle Fishing
Luxury & Special Occasions
Luxury & Special Occasions
Museums
Museums
Outdoor Activities
Outdoor Activities
Parasailing
Parasailing
Private & Custom Tours
Private & Custom Tours
Private Charters
Sailing
Sailing
Scooter Rentals
Scooter Rentals
Scuba Diving
Scuba Diving
Scuba Instruction
Scuba Instruction
Shore Excursions
Shore Excursions
Sightseeing Tickets & Passes
Sightseeing Tickets & Passes
Sightseeing Tours
Snorkeling
Snorkeling
Sunset Cruises
Tours & Sightseeing
Tours & Sightseeing
Transfers & Ground Transport
Trolley Tours
Unique Experiences
Unique Experiences
Vehicle Rentals
Vehicle Rentals
Walking & Biking Tours
Walking & Biking Tours
Walking Tours
Water Sports
Water Sports
Water Tours
When are you traveling?
Filter
Languages Clear
Time of Day Clear
9
10
8
Duration Clear
0
12
7
0
0
Price Clear
$0 $500+
Specials Clear
16
14
0
0
0
Features Clear
1
16
17
1
10
Accessibility Clear
0
7
14
Families Clear
10
4
9
Rating Clear
17
18
18

Key West Tours

18 Results
Sort by:
Featured
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out

    Key West Sail, Snorkel, Kayak with Sunset Option

    2,338

    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

    2,338

    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

    1,442

    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

    281

    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

    120

    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

    126

    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

    1,528

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

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

    215

    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
  • Famous Key West Sunset Sail
    Likely to Sell Out

    Famous Key West Sunset Sail

    825

    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

    495

    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
  • Reef Snorkel & Sail Adventure – Morning
    Likely to Sell Out

    Reef Snorkel & Sail Adventure – Morning

    134

    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

    418

    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
  • Half-Day Cruise with Kayaking and Snorkeling
    Likely to Sell Out

    Half-Day Cruise with Kayaking and Snorkeling

    2,279

    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
    $122.08
    Details
    from
    $122.08
    Details
  • Small-Group Sunset Sail with Wine
    Likely to Sell Out

    Small-Group Sunset Sail with Wine

    1,442

    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
    $133.89
    Details
    from
    $133.89
    Details
  • Key West Classic Day Sail Aboard America 2.0
    Likely to Sell Out

    Key West Classic Day Sail Aboard America 2.0

    185

    Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...
    Read More

     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $73.10
    Details
    from
    $73.10
    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 →

Things To Do In Key West

Lowest Price Guarantee

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

We guarantee the lowest price on all the tours available to book on our site. We'll refund the difference if you find the exact tour cheaper online until 48 hours before your tour starts.

We Make It Easy!

Gather your information

Locate your Tours of Key West Booking Number and the proof of the lower price you found.

Send it to us

Email [email protected] with the documents, your name, and your home address.

We'll review

We'll review your materials and get in touch as soon as possible.

Receive your refund

If everything checks out, we'll refund you the price difference.

Refund Terms & Conditions

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.
  • Tours of Key West promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same tour, 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 Tours of 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 tour into one or more parts sold separately.
  • Tours of 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 Tours of Key West.

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.

Chat with us

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Concierge