Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 128 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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Exellent1,809 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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Superb4,681 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
Likely to Sell Out Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
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Florida
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Superb3,746 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
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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Florida
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Exellent668 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
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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Florida
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Exellent377 reviews4.5
Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. â€....
Buccaneer Pirate Cruise in Destin
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family! Enjoy a fun cruise with interactive pirate-themed activities, entertainment, and treasure hunts. Take in the beauty of the Emeral... More
Likely to Sell Out Buccaneer Pirate Cruise in Destin
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Florida
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Superb118 reviews4.8
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
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
Likely to Sell Out Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
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Florida
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Superb1,998 reviews4.9
The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which....
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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Florida
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Superb124 reviews4.6
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
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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Florida
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Superb171 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
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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Florida
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Superb1,444 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
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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Florida
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Superb747 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
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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Florida
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Exellent453 reviews4.4
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
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
Likely to Sell Out St. Augustine Live Music Sail with Drinks & Sunset Option
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Florida
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Superb362 reviews4.7
Come aboard our spacious state-of-the-art catamaran and choose your perfect St Augustine experience!....
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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Florida
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Superb220 reviews4.8
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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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Florida
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Superb957 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
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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Florida
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Superb558 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Bimini or Grand Bahama Island Day Cruise
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Florida! Picture this: pristine white beaches, crystal-clear turquoise waters, and tons of fun activities waiting for you. We'll pick... More
Likely to Sell Out Bimini or Grand Bahama Island Day Cruise
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Florida
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Good19 reviews3.4
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....
Likely to Sell Out Key West Dolphin and Snorkel Experience
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Florida
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Exellent356 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
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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Florida
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Exellent381 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
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
Likely to Sell Out Sunset Catamaran Cruise in Ft. Lauderdale
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Florida
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Superb702 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....