Sailing Trips in Key West
Top 10 Best Key West Sailing Trips
Found 40 Sailing Trips activities in Key West. Sort by Popularity.Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
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Key West
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Superb3,469 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
Key West Champagne Sunset Catamaran Cruise
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 included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail thr... More
Likely to Sell Out Key West Champagne Sunset Catamaran Cruise
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Key West
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Superb582 reviews4.7
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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 West, as you sail by Mallory Square, Sunset Pier, Sand K... More
Likely to Sell Out Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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Key West
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Superb767 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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 sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Likely to Sell Out Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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Key West
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Superb1,324 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Key West Reef Morning Snorkeling with Breakfast and Mimosas
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 Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More
Likely to Sell Out Key West Reef Morning Snorkeling with Breakfast and Mimosas
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Key West
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Exellent563 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Sunset Sail in Key West with Beverages Included
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 to detail on our sunset cruise is legendary. Being out on the... More
Likely to Sell Out Sunset Sail in Key West with Beverages Included
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Key West
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Superb893 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Key West Signature Sunset Sail with Live Music, Open Bar & Food
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music • Great Appetizers Welcome aboard Key West's newest catamaran, the "Sandie Cat" as we literally... More
Likely to Sell Out Key West Signature Sunset Sail with Live Music, Open Bar & Food
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Key West
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Exellent306 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More
Likely to Sell Out Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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Key West
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Superb679 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
Likely to Sell Out Key West Dolphin and Snorkel Experience
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Key West
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Exellent325 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Key West's Favorite Afternoon Dolphin Sail
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More
Likely to Sell Out Key West's Favorite Afternoon Dolphin Sail
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Key West
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Superb110 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant sailing experience. Guests board a spacious Fury Catamaran, part of the largest luxury fleet in the Florida Keys, and sail to North Ame... More
Likely to Sell Out Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail
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Key West
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Exellent366 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Key West Reef Snorkel & Sail Adventure
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 the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More
Likely to Sell Out Key West Reef Snorkel & Sail Adventure
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Key West
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Superb535 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Key West Sailing & Snorkeling: A Reef Adventure
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 the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More
Likely to Sell Out Key West Sailing & Snorkeling: A Reef Adventure
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Key West
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Superb168 reviews4.8
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Key West Afternoon Reef Snorkeling with Open Bar
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 West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More
Likely to Sell Out Key West Afternoon Reef Snorkeling with Open Bar
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Key West
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Exellent407 reviews4.4
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico and the Atlantic Ocean meet in a symphony of beauty and tranquility. Your day begins as you board a luxurious catamaran, your vess... More
Likely to Sell Out Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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Key West
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Exellent75 reviews4.5
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Key West Historic Schooner When And If Sunset Cruise
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More
Likely to Sell Out Key West Historic Schooner When And If Sunset Cruise
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Key West
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Superb102 reviews4.8
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner....
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More
Likely to Sell Out Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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Key West
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Superb941 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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 enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
Likely to Sell Out Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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Key West
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Superb146 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More
Likely to Sell Out Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
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Key West
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Superb86 reviews4.9
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
Classic Key West Schooner Sunset Sail with Full Open Bar
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Ke... More
Likely to Sell Out Classic Key West Schooner Sunset Sail with Full Open Bar
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Key West
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Superb200 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....