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  • 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

    1265

    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  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

    140

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

    282

    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  Free Cancellation  Instant Confirmation
    $199.95
    $169.95
    Details
    $199.95
    $169.95
    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

    265

    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...
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     90 minutes (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $49.95
    Details
    Best Rate
    $49.95
    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

    585

    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  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Details
    Best Rate
    $99.95
    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

    686

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

    Key West Backcountry Safari

    686

    Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....
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     6.5 or 4.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $120
    $115
    Details
    $120
    $115
    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

    252

    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  Free Cancellation  Instant Confirmation
    Best Rate
    $109
    Details
    Best Rate
    $109
    Details
  • 1-Hour Interactive Pirate Cruise in Ft. Lauderdale (arrive 30 minutes early)
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    1-Hour Interactive Pirate Cruise in Ft. Lauderdale (arrive 30 minutes early)

    322

    Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along...
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     1 hour  Free Cancellation  Instant Confirmation
    from
    $24.83
    Details
    from
    $24.83
    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

    106

    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
    $79.95
    Details
    from
    $79.95
    Details
  • Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

    958

    The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $52.43
    Details
    from
    $52.43
    Details
  • Key West Sunset Snorkel with Unlimited Draft Beer & Wine
    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

    38

    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
    $59.95
    Details
    from
    $59.95
    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

    96

    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...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $74.95
    Details
    from
    $74.95
    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

    4.5 Hours • All Ages • Sodas, beer, wine & snacks included...
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     4.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $2,399
    $2,269.69
    Details
    $2,399
    $2,269.69
    Details
  • Sunset & Dolphin Catamaran Cruise with Island Time
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Sunset & Dolphin Catamaran Cruise with Island Time

    370

    The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $52.43
    Details
    from
    $52.43
    Details
  • Champagne Sunset Cruise in Ft. Lauderdale
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Champagne Sunset Cruise in Ft. Lauderdale

    262

    A perfect way to end the day relaxing on the Atlantic ocean taking in the breathtaking views with Fort Lauderdale Charters Cast Away the Day...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $85
    Details
    from
    $85
    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

    253

    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
  • Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
    Likely to Sell Out

    Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

    93

    Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall...
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     1 hour 30 minutes  Instant Confirmation
    from
    $54.50
    Details
    from
    $54.50
    Details
  • Panama City Beach Sunset Catamaran Sail on The Privateer
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Panama City Beach Sunset Catamaran Sail on The Privateer

    184

    If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the “Privateer”, our...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $40
    Details
    from
    $40
    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

    129

    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
    $46.94
    Details
    from
    $46.94
    Details
  • Key West Afternoon Reef Snorkeling with Open Bar

    Key West Afternoon Reef Snorkeling with Open Bar

    82

    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
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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 USA Sailing Trips?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best USA Sailing Trips are:

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

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly USA Sailing Trips are:

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Q: Which USA Sailing Trips have Instant Confirmation?

A: USA Sailing Trips with Instant Confirmation include:

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Q: Which USA Sailing Trips have Free Cancellation?

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

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

A: No problem. These USA Sailing Trips include Hotel Pickup:

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Q: Got any more USA trip ideas?

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

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

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

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