Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 128 Sailing Trips activities in Florida. Sort by Popularity. - Page 2Sunset 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
Likely to Sell Out Sunset Sail in Miami: Complimentary Champagne Toast
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Florida
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Superb230 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great way to have fun in the sun and enjoy the best of what Panama City Beach has to offer! Cruise over to Shell Island where you and the... More
Likely to Sell Out Shell Island Snorkel and Dolphin Catamaran Cruise with Island Tim....
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Florida
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Superb4,361 reviews4.9
The 3-Hr Shell Island Snorkel & Dolphin Cruise aboard the Island Time Sailing Catamaran is a great w....
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
Likely to Sell Out 1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
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Florida
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Superb1,481 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
Nights of Lights Sailboat Tour at St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More
Likely to Sell Out Nights of Lights Sailboat Tour at St Augustine Sailing
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Florida
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Superb18 reviews5
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....
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
Likely to Sell Out Classic Key West Schooner Sunset Sail with Full Open Bar
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Florida
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Superb208 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Panama City Beach Sunset Catamaran Sail on The Privateer
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer, our 78-passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mex... More
Likely to Sell Out Panama City Beach Sunset Catamaran Sail on The Privateer
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Florida
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Superb709 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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
Likely to Sell Out 2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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Florida
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Superb97 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
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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Superb692 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
Likely to Sell Out
Ft Myers Beach 2 Hour 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
Free Cancellation
(Saving 25% )
Likely to Sell Out Ft Myers Beach 2 Hour Tiki Pub Fun in the Sun Dolphin Cruise
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Florida
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Superb80 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Free Cancellation
(Saving 25% )
Schooner Clearwater- Sailing Cruise-Clearwater Beach
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More
Likely to Sell Out Schooner Clearwater- Sailing Cruise-Clearwater Beach
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Florida
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Superb227 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....
Fort Lauderdale Sailing Charter
You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as the “Venice of America." The New River offers a blend of natural beauty, luxurious homes, and fascinating history. Your adventure ... More
Likely to Sell Out Fort Lauderdale Sailing Charter
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Florida
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Superb384 reviews5
You Embark on an unforgettable journey starting in Fort Lauderdale on our New River also known as th....
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
Likely to Sell Out 4-Hour Fort Lauderdale Sailing Charter
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Florida
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Superb311 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
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
Likely to Sell Out Private Sailing Tour through the Ten Thousands Islands
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Florida
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Superb150 reviews4.9
If you like to sail but have never been on a stiletto catamaran then are missing out! The stilettos ....
Private Tour
Dolphin Adventure Sail in Cocoa Beach
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for an unforgettable journey through the Banana River Lagoon! Glide across calm waters on our spacious catamaran as you encounter pla... More
Private Tour
Likely to Sell Out Dolphin Adventure Sail in Cocoa Beach
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Florida
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Superb163 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
Private Tour
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
Private Tour
Likely to Sell Out Buccaneer Pirate Cruise in Destin
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Florida
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Superb95 reviews4.9
Board a pirate ship in Destin and set out on a swashbuckling adventure perfect for the whole family!....
Private Tour
Likely to Sell Out
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, 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 pals on ou... More
Free Cancellation
Private Tour
(Saving 20% )
Likely to Sell Out Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
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Florida
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Superb26 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
Free Cancellation
Private Tour
(Saving 20% )
Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We have made a commitment to sustainability and having a minimal impact on the environment ! It is a wholesome adventure that will le... More
Private Tour
Likely to Sell Out Half-Day Private Guided Sailing Adventure of Miami's Biscayne Bay
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Florida
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Superb12 reviews4.9
We are the only boat tour 100% powered by the wind and paddle. We don't use engines of any kind. We ....
Private Tour
50ft Luxury Yacht Tour in Miami Beach Captain, Fun & Party!
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate like never before. This VIP experience is designed for fun, style, and unforgettable memories with your group. Adventure Highlig... More
Private Tour
Likely to Sell Out 50ft Luxury Yacht Tour in Miami Beach Captain, Fun & Party!
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Florida
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Exellent45 reviews4.3
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....
Private Tour
Bimini or Grand Bahama Island by Ferry
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
Private Tour
Likely to Sell Out Bimini or Grand Bahama Island by Ferry
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Florida
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Very Good15 reviews3.7
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....
Private Tour
Key West Dolphin Watch and Sunset Sail on Catamaran
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of wind. This tour is perfect for all ages and offers a wide-open, unob... More
Private Tour
Likely to Sell Out Key West Dolphin Watch and Sunset Sail on Catamaran
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Florida
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Superb32 reviews4.7
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lig....
Private Tour