Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 119 Sailing Trips activities in Florida. Sort by Popularity. - Page 2
Key West Dolphin and Snorkel Experience
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Florida
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Exellent296 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
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
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Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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Florida
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Superb920 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Free Cancellation
(Saving 10% )
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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Exellent388 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 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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Exellent63 reviews4.5
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....

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
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Shallow Water Snorkeling and Dolphin Watching in Key West
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Florida
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Superb458 reviews4.6
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....
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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

Classic Key West Schooner Sunset Sail with Full Open Bar
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Florida
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Superb182 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Sunset Sail Aboard the 47 ft Daydreams Sailboat
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More

Sunset Sail Aboard the 47 ft Daydreams Sailboat
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Florida
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Superb21 reviews4.9
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....
Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play party games and have a blast! With a cozy capacity for 25, choose between mingling with new pal... More

Ft Myers Beach Tiki Pub Fun in the Sun Dolphin Cruise
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Florida
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Superb66 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More

Suncoast Sailing's Sunset Sailing Experience!
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Florida
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Superb234 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Sunset Sail in Miami: Complimentary Champagne Toast
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida's finest highlights upon our comfortable 80 ft catamaran a... More

Sunset Sail in Miami: Complimentary Champagne Toast
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Florida
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Superb227 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
4-Hour Fort Lauderdale Sailing Charter
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

4-Hour Fort Lauderdale Sailing Charter
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Florida
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Superb300 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
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

Buccaneer Pirate Cruise in Destin
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Florida
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Superb82 reviews4.9
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
Private Sailing Tour through the Ten Thousands Islands
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos where built in the early 80s and are known through out the sailing community as the fastest, driest, beachable catamaran on the ma... More
Private Tour

Private Sailing Tour through the Ten Thousands Islands
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Florida
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Superb143 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
Private Tour
Sail & Splash Excursion in Ft. Lauderdale
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More
Private Tour

Sail & Splash Excursion in Ft. Lauderdale
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Florida
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Superb270 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
Private Tour
Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More
Private Tour

Sunset Sail Cruise in Key West
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Florida
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Superb240 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Miami Beach experience. Connect with nature, discover new landscapes, & create lasting memories as you explore the stunning coastline... More
Private Tour

Miami Beach Luxury Yacht Adventure: Explore Stunning Coastline
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Florida
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Superb23 reviews4.8
Embark on a private yacht journey, perfect for families, couples, & adventurers seeking a unique Mia....
Private Tour
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along Florida’s Intracoastal Waterway that’s fun for the whole family! T... More
Private Tour

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
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Florida
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Superb1,454 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
Private Tour
Sunset Catamaran Sail in Cocoa Beach
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning evening on the serene waters of the Banana River Lagoon. Our Sunset Sail is the perfect way to relax and take in the beauty of Florida... More
Private Tour

Sunset Catamaran Sail in Cocoa Beach
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Florida
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Superb162 reviews4.9
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private Tour
Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews on Google. What you will get: Nature Immersion: Encounter dolphins, turtles, manatees, and more as you explore Miami's waters Cel... More
Private Tour

Private Boat Tour - Snorkeling, Star Island & Dolphin Spotting
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Florida
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Superb56 reviews4.7
DolphinWaterSport is renowned for providing exceptional experiences. With a 4.9 rate & +800 reviews ....
Private Tour
Ultimate Party in Miami : Boat Party, Party Bus & Nightclub
This is not just another night out, it’s Miami’s nightlife on the water. Step aboard a spacious double-decker boat transformed into a moving nightclub with a live DJ, dazzling lights, and a vibrant atmosphere. As the sun sets,... More
Private Tour

Ultimate Party in Miami : Boat Party, Party Bus & Nightclub
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Florida
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Good16 reviews3.1
This is not just another night out, it’s Miami’s nightlife on the water. Step aboard a spacious ....
Private Tour