Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 120 Sailing Trips activities in Florida. Sort by Popularity.Miami Millionaires Sightseeing Cruise
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More
Miami Millionaires Sightseeing Cruise
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Florida
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Exellent1,923 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes approximately 1 hour of snorkeling at Shell Island, where... More
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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Florida
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Superb4,864 reviews4.9
Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboa....
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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Florida
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Superb3,796 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
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
Key West Signature Sunset Sail with Live Music, Open Bar & Food
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Florida
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Exellent392 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in Panama City Beach, FL. Enjoy a rum punch while cruising along the beautiful Gulf Coa... More
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
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Florida
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Superb2,056 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
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
Key West Reef Morning Snorkeling with Breakfast and Mimosas
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Florida
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Exellent705 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Buccaneer Pirate Cruise in Destin
Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew stays in full character, pulling the younger buccaneers into pirate training, sword fights, water gun battles, and a search for un... More
Buccaneer Pirate Cruise in Destin
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Florida
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Superb135 reviews4.8
Take to the pirate life aboard Destin's only pirate ship. From the moment you step aboard, our crew ....
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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Florida
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Superb167 reviews4.7
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Key West Dolphin and Snorkel Experience
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Florida
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Exellent365 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
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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Florida
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Exellent468 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 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
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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Florida
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Superb190 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
St. Augustine Live Music Sail with Drinks & Sunset Option
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience! Opt for a two-hour live music sunset sail with all sails raised, or unwind on a 90-minute After Dark Live Music Cruise (no sailin... More
St. Augustine Live Music Sail with Drinks & Sunset Option
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Florida
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Superb386 reviews4.7
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....
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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Florida
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Superb974 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
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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Florida
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Superb1,466 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Sunset Catamaran Cruise in Ft. Lauderdale
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach as the sun slips slowly behind the lights of the city. This evening cruise calls for sun ... More
Sunset Catamaran Cruise in Ft. Lauderdale
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Florida
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Superb706 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
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
Key West's Favorite Afternoon Dolphin Sail
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Florida
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Superb211 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
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
Key West Sailing & Snorkeling: A Reef Adventure
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Florida
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Superb238 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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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Florida
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Superb757 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
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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Florida
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Exellent384 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
Bimini or Grand Bahama Island Day Cruise
Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear turquoise waters, and vibrant culture. Turn your getaway ... More
Bimini or Grand Bahama Island Day Cruise
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Florida
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Good19 reviews3.4
Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands....