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Key West Cruises, Sailing & Water Tours

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Key West Tours

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  • Key West Shark and Wildlife Catamaran Tour
    Likely to Sell Out

    Key West Shark and Wildlife Catamaran Tour

    2,672

    This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $99
    Details
    from
    $99
    Details
  • Reef Snorkel & Sail Adventure – Afternoon
    Likely to Sell Out

    Reef Snorkel & Sail Adventure – Afternoon

    505

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Famous Key West Sunset Sail

    Famous Key West Sunset Sail

    853

    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Champagne Celebration Sunset Cruise
    Likely to Sell Out

    Champagne Celebration Sunset Cruise

    885

    Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...
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     2 hours  Instant Confirmation
    from
    $98.01
    Details
    from
    $98.01
    Details
  • Reef Snorkel & Sail Adventure – Morning
    Likely to Sell Out

    Reef Snorkel & Sail Adventure – Morning

    142

    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

    425

    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...
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     4 hours  Instant Confirmation
    from
    $98.01
    Details
    from
    $98.01
    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...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $73.10
    Details
    from
    $73.10
    Details
  • Half-Day Cruise with Kayaking and Snorkeling
    Likely to Sell Out

    Half-Day Cruise with Kayaking and Snorkeling

    2,322

    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...
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     4 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $105
    Details
    from
    $105
    Details
  • Small-Group Sunset Sail with Wine
    Likely to Sell Out

    Small-Group Sunset Sail with Wine

    1,467

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $115
    Details
    from
    $115
    Details
  • Key West Wind & Wine Private Charter

    Key West Wind & Wine Private Charter

    1,467

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Tours of Key West three years running. See the...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $3,499
    Details
    Best Rate
    $3,499
    Details
  • All Inclusive Water Adventure Excursion in Key West
    Likely to Sell Out

    All Inclusive Water Adventure Excursion in Key West

    2,322

    Tours of Key West is the only tour operator in Key West offering sailing excursions on a historic schooner into the remote backcountry of the...
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     6 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $145
    Details
    from
    $145
    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

    558

    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...
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     6 hours (approx.)  Instant Confirmation
    $124.95
    $119.95
    Details
    $124.95
    $119.95
    Details
  • Key West Sunset Cocktail Cruise

    Key West Sunset Cocktail Cruise

    156

    “The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure...
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     2 hours  Instant Confirmation
    from
    $65
    Details
    from
    $65
    Details
  • Looe Key Snorkel

    Looe Key Snorkel

    422

    Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef...
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     3 hours  Free Cancellation
    from
    $575
    Details
    from
    $575
    Details
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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 Tours of Key West 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 Tours of Key West 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 →

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Lowest Price Guarantee

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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.

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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

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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.

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