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Key West Sailing Trips

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Key West Tours

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

    Key West Sail, Snorkel, Kayak with Sunset Option

    2,370

    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
    Details
  • Key West Backcountry Safari
    Likely to Sell Out

    Key West Backcountry Safari

    2,370

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

    1,456

    Wind & Wine has been the #1 rated sunset sail on City Boat Tours 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
    Details
  • Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

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

    3,252

    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...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $79.95
    Details
    Best Rate
    $79.95
    Details
  • Key West Original Full-Day Watersports Adventure
    Special Offer

    Key West Original Full-Day Watersports Adventure

    738

    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...
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     6 hours (approx.)  Free Cancellation  Instant Confirmation
    $199.69
    $169
    Details
    $199.69
    $169
    Details
  • Key West Catamaran Dolphin Watch & Sunset Sail

    Key West Catamaran Dolphin Watch & Sunset Sail

    643

    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...
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     2 hours 30 minutes (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $89.95
    Details
    Best Rate
    $89.95
    Details
  • Sunset Sip and Sail Key West with Open Bar and Live Music
    Likely to Sell Out

    Sunset Sip and Sail Key West with Open Bar and Live Music

    287

    Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...
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     2 hours  Free Cancellation
    from
    $72
    Details
    from
    $72
    Details
  • Key West Dolphin and Snorkel Experience
    Likely to Sell Out

    Key West Dolphin and Snorkel Experience

    275

    The City Boat Tours Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    Details
    from
    $69.95
    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

    1,528

    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...
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     2 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Details
    Best Rate
    $99.95
    Details
  • Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
    Likely to Sell Out

    Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine

    137

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    Details
    from
    $69.95
    Details
  • Key West Snorkeling with Breakfast and Unlimited Mimosas

    Key West Snorkeling with Breakfast and Unlimited Mimosas

    506

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $35
    Details
    from
    $35
    Details
  • Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
    Likely to Sell Out

    Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

    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...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $116.10
    Details
    from
    $116.10
    Details
  • Key West Schooner Backcountry Eco-Tour

    Key West Schooner Backcountry Eco-Tour

    215

    Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...
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     5 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $109.95
    Details
    Best Rate
    $109.95
    Details
  • Sunset Sail in Key West with Beverages Included
    Likely to Sell Out

    Sunset Sail in Key West with Beverages Included

    846

    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
  • Key West Reef Snorkel & Sail Adventure
    Likely to Sell Out

    Key West Reef Snorkel & Sail Adventure

    501

    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
  • Key West Afternoon Reef Snorkeling with Open Bar
    Likely to Sell Out

    Key West Afternoon Reef Snorkeling with Open Bar

    362

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $59.95
    Details
    from
    $59.95
    Details
  • Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
    Likely to Sell Out

    Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

    883

    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
  • Key West Sailing & Snorkeling: A Reef Adventure
    Likely to Sell Out

    Key West Sailing & Snorkeling: A Reef Adventure

    139

    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
  • Shallow Water Snorkeling and Dolphin Watching in Key West
    Likely to Sell Out

    Shallow Water Snorkeling and Dolphin Watching in Key West

    423

    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
    $98.01
    Details
    from
    $98.01
    Details
  • Key West Day Sail on Schooner America 2.0 with 2 Drinks
    Likely to Sell Out

    Key West Day Sail on Schooner America 2.0 with 2 Drinks

    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
  • Sunset Sail Cruise in Key West
    Likely to Sell Out

    Sunset Sail Cruise in Key West

    232

    Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's...
    Read More

     2 hours  Free Cancellation  Instant Confirmation
    from
    $95
    Details
    from
    $95
    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 Sailing Trips?

A: According to verified reviews on City Boat Tours 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 City Boat Tours 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: 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 →

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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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Gather your information

Locate your City Boat Tours Booking Number and the proof of the lower price you found.

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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.
  • City Boat Tours 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 City Boat Tours 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.
  • City Boat Tours 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 City Boat Tours.

Sorting, ranking, and search results

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City Boat Tours 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 City Boat Tours 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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