Sailing Trips in Key West
Top 10 Best Key West Sailing Trips
Found 48 Sailing Trips activities in Key West. Sort by Popularity. - Page 3Schooner Bloody Mary Day Sail with Full Open Bar in Key West
Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water’s surface or circling in the blue sky above you. P... More

Schooner Bloody Mary Day Sail with Full Open Bar in Key West
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Key West
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Superb9 reviews4.9
Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in pa....
Private Sunset Sail in Key West Florida
Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More
Private Tour

Private Sunset Sail in Key West Florida
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Key West
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Superb9 reviews4.9
Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just ....
Private Tour
2-hour Customizable Private Day Sail in Key West
This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon one of our historic schooners. This trip has a capacity of up to 26 people, and a selection of sodas, beer, and wine are included... More
Private Tour

2-hour Customizable Private Day Sail in Key West
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Key West
This 2-hour, customizable day sail allows for you to experience the pristine Florida Keys water upon....
Private Tour
Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats
Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More
Private Tour

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats
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Key West
Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water ....
Private Tour
Private Afternoon Snorkel with Sunset Sail in Key West
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More
Private Tour

Private Afternoon Snorkel with Sunset Sail in Key West
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Key West
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Superb4 reviews5
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that sp....
Private Tour
Key West Haunted Night Sail on Schooner America 2.0
Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under the Key West night sky. During this night boat ride, we'll cruise through the waters of Key West while listening to mysterious t... More
Private Tour

Key West Haunted Night Sail on Schooner America 2.0
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Key West
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Superb4 reviews5
Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under....
Private Tour
Private 2-Hour Wind and Wine Sunset Sail in Key West
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More
Private Tour

Private 2-Hour Wind and Wine Sunset Sail in Key West
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Key West
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Superb81 reviews4.9
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from ....
Private Tour
Key West Wreckers Race Aboard Schooner America 2.0
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More
Private Tour

Key West Wreckers Race Aboard Schooner America 2.0
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Key West
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Superb9 reviews4.9
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse abo....
Private Tour