Sailing Trips in Key West
Top 10 Best Key West Sailing Trips
Found 45 Sailing Trips activities in Key West. Sort by Popularity.Key West Sunset Sail with Full 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 Full Bar, Live Music and Hors D'oeuvres
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Key West
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Superb3,132 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
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

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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Key West
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Superb685 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
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

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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Key West
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Superb619 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
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

Sunset Sail in Key West with Beverages Included
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Key West
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Superb789 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
Key West Snorkeling with Breakfast and Unlimited 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

Key West Snorkeling with Breakfast and Unlimited Mimosas
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Key West
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Exellent501 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
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

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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Key West
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Superb1,208 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
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

Key West Reef Snorkel & Sail Adventure
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Key West
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Superb508 reviews4.7
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

Key West Afternoon Reef Snorkeling with Open Bar
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Key West
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Exellent340 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More

Key West Sunset Sail Aboard Legendary Schooner Appledore
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Key West
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Superb147 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Adults only Sunset Cruise from Key West with Champagne
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 in the tour price are the house champagne Chandon Brut, 7 premium red and whit... More

Adults only Sunset Cruise from Key West with Champagne
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Key West
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Superb887 reviews4.9
Get out on Key West’s beautiful shallow waters on the Adults Only sunset cruise, to sip Moët & Ch....
Sunset Sip and Sail Key West with Open Bar and Live Music
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

Sunset Sip and Sail Key West with Open Bar and Live Music
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Key West
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Exellent259 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
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

Key West Rum and Reggae:Reef Snorkel Adventure and Sunset Sail
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Key West
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Exellent347 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....

Key West Dolphin and Snorkel Experience
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Key West
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Exellent269 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Key West Sunset Snorkel with Unlimited Draft 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

Key West Sunset Snorkel with Unlimited Draft Beer & Wine
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Key West
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Superb116 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Shallow Water Snorkeling and Dolphin Watching in Key West
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 - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More

Shallow Water Snorkeling and Dolphin Watching in Key West
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Key West
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Superb436 reviews4.6
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....
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

Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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Key West
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Superb24 reviews4.8
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world with a blue sea too alluring to ignore. I arrived to Key West in 2005. Now I have 10+ years of experience studying Biology and bein... More

Mangrove Kayak + Snorkel & Sunset Sail hosted by Honest Eco
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Key West
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Superb150 reviews5
I founded and own HONEST ECO. With Kentucky bluegrass roots and a B.S. in Biology, I found a world w....
Private Key West Sandbar and Paddle by Boat
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats and wildlife refuges as well as spot an abundance of marine birds and sea life. Padd... More
Private Tour

Private Key West Sandbar and Paddle by Boat
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Key West
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Superb31 reviews4.9
Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may....
Private Tour
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
Private Tour

Classic Key West Schooner Sunset Sail with Full Open Bar
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Key West
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Superb67 reviews5
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Private Tour
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
Private Tour

Key West Sailing & Snorkeling: A Reef Adventure
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Key West
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Superb127 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Private Tour