Top Key West Cruises, Sailing & Water Tours

When are you traveling?
Filter
Price Clear
$0 $500+
Popular Clear
Rating Clear
Duration Clear
Time of Day Clear

Key West Tours

Attractions

Guides

Calendar

94 Results
Sort by:
Featured
  • Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

    1439

    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...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    Best Rate
    $74.95
    Details
    Best Rate
    $74.95
    Details
  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Wind & Wine Sunset Sail

    154

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Destinations three years running....
    Read More

     2 Hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    Details
    $109
    $99
    Details
  • Key West Original Full-Day Watersports Adventure
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Original Full-Day Watersports Adventure

    304

    This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...
    Read More

     6 hours  Free Cancellation  Instant Confirmation
    $199.95
    $169.95
    Details
    $199.95
    $169.95
    Details
  • Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

    105

    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 Champagne Catamaran Cruise
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Champagne Catamaran Cruise

    294

    Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy...
    Read More

     90 minutes (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $49.95
    Details
    Best Rate
    $49.95
    Details
  • Key West Sunset Dinner Cruise with Tropical Buffet Dinner
    Likely to Sell Out

    Key West Sunset Dinner Cruise with Tropical Buffet Dinner

    717

    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....
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $92.95
    Details
    from
    $92.95
    Details
  • Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

    Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

    624

    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...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Details
    Best Rate
    $99.95
    Details
  • Key West Backcountry Safari
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Backcountry Safari

    791

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

     6.5 or 4.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $120
    $115
    Details
    $120
    $115
    Details
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sail, Snorkel, Kayak with Sunset Option

    791

    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 Catamaran Dolphin Watch & Sunset Sail
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Catamaran Dolphin Watch & Sunset Sail

    298

    Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...
    Read More

     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    Best Rate
    $109
    Details
    Best Rate
    $109
    Details
  • Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Sunset Sip and Sail with Open Bar, Live Music, and Appetizers from Key West

    128

    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
  • The Key West Dolphin & Snorkel Experience
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    The Key West Dolphin & Snorkel Experience

    117

    The Cool Destinations Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $74.95
    Details
    from
    $74.95
    Details
  • Key West Sunset Snorkel with Unlimited Draft Beer & Wine
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Snorkel with Unlimited Draft Beer & Wine

    41

    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
    $59.95
    Details
    from
    $59.95
    Details
  • Key West Mangrove Kayak Eco Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Mangrove Kayak Eco Tour

    782

    Along with your experienced guide you will paddle at a relaxing pace and explore the shallow, calm, blue-green waters of the back country of Key...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $60
    Details
    from
    $60
    Details
  • Private Key West Morning Sail, Snorkel & Kayak Excursion
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Private Key West Morning Sail, Snorkel & Kayak Excursion

    New To The Site!

    4.5 Hours • All Ages • Sodas, beer, wine & snacks included...
    Read More

     4.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $2,399
    $2,269.69
    Details
    $2,399
    $2,269.69
    Details
  • Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

    268

    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
  • Key West Dolphin Watch & Snorkel with FREE shuttle to location
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Dolphin Watch & Snorkel with FREE shuttle to location

    102

    Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....
    Read More

     3.5 Hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $99
    Details
    Best Rate
    $99
    Details
  • Key West Snorkeling with Breakfast and Unlimited Mimosas
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Snorkeling with Breakfast and Unlimited Mimosas

    191

    Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $46.94
    Details
    from
    $46.94
    Details
  • Key West Afternoon Reef Snorkeling with Open Bar
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Afternoon Reef Snorkeling with Open Bar

    99

    Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key...
    Read More

     3 hours  Free Cancellation  Instant Confirmation
    from
    $52.80
    Details
    from
    $52.80
    Details
  • Adults only Champagne Celebration Sunset Cruise from Key West
    Likely to Sell Out

    Adults only Champagne Celebration Sunset Cruise from Key West

    408

    Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Chandon champagne while enjoying the sunset. Included...
    Read More

     2 hours  Instant Confirmation
    from
    $81.40
    Details
    from
    $81.40
    Details
  • Key West Sunset Sail Aboard Schooner
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Sail Aboard Schooner

    624

    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
    $111.80
    Details
    from
    $111.80
    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 Cruises, Sailing & Water Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Key West Cruises, Sailing & Water Tours are:

Q: What are the best kid-friendly options for Key West Cruises, Sailing & Water Tours Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Key West Cruises, Sailing & Water Tours are:

View all kid-friendly Tours →

Q: Which Key West Cruises, Sailing & Water Tours have Instant Confirmation?

A: Key West Cruises, Sailing & Water Tours with Instant Confirmation include:

View all Tours with Instant Confirmation →

Q: Which Key West Cruises, Sailing & Water Tours have Free Cancellation?

A: Key West Cruises, Sailing & Water Tours 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 Cruises, Sailing & Water Tours include Hotel Pickup?

A: No problem. These Key West Cruises, Sailing & Water Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Q: Got any more Key West trip ideas?

A: We sure do. Check out our curated lists of hand-picked Key West Tours.

View all Key West Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Key West?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Key West are:

View all tour styles in Key West →