Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 118 Sailing Trips activities in Florida. Sort by Popularity. - Page 2Sunset Dolphin Sail Aboard the Privateer Catamaran
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
Sunset Dolphin Sail Aboard the Privateer Catamaran
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Florida
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Superb747 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
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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Superb249 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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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Superb267 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
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
Key West Reef Snorkel & Sail Adventure
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Florida
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Superb568 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 + Reef Snorkel & Sandbar
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • Guided Snorkeling Your mate hops in the water with you and points out animals and shows yo... More
Key West: Sunset Sail + Reef Snorkel & Sandbar
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Florida
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Superb55 reviews5
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....
Sunset Dolphin Sail Aboard the Footloose Catamaran
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on SV Footloose, our 38 passenger catamaran, with Paradise Adventures! This breathtaking sunset sail along the Gulf of Mexico ... More
Sunset Dolphin Sail Aboard the Footloose Catamaran
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Florida
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Superb482 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
Beach Island Shelling Cruise to Keewaydin Island Tour
Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommodate up to 44 passengers. Cruise along the Gordon River in Naples Bay and head out to Keewaydin Island, a 7-mile barrier island, wit... More
Beach Island Shelling Cruise to Keewaydin Island Tour
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Florida
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Superb105 reviews4.9
Enjoy a family favorite cruise aboard the Sweet Liberty, a 53' sailing catamaran, that can accommoda....
Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. We have been sailing the Biscayne Bay for over 15 years, just for the fun of it. We started this eco-tour in 2018 to share the ama... More
Likely to Sell Out Sail Biscayne Bay: An Intimate Eco-Adventure with Snorkeling
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Florida
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Superb468 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
Sunset Sailing Cruise Aboard Schooner Clearwater-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. *Partic... More
Likely to Sell Out Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
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Florida
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Superb278 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wil....
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
Likely to Sell Out Dolphin Adventure Sail in Cocoa Beach
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Florida
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Superb231 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
Miami Private Yacht Celebration Cruise with Captain
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 Miami Private Yacht Celebration Cruise with Captain
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Florida
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Superb65 reviews4.6
Ready for the party of a lifetime? Step aboard our luxurious Yacht Tour in Miami Beach and celebrate....
Private Tour
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
Private Tour
Likely to Sell Out 4-Hour Fort Lauderdale Sailing Charter
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Florida
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Superb323 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
Private Tour
Southwest Florida Sunset Sail
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The sunset hours are a magical time to be out on the water. With the winds calm, the sun turns g... More
Private Tour
Likely to Sell Out Southwest Florida Sunset Sail
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Florida
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Superb513 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
Private Tour
Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters... More
Private Tour
Likely to Sell Out Fins Up - Dolphin & Island Sandbar Adventure in Clearwater Beach
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Florida
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Exellent74 reviews4.5
Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Do....
Private Tour
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
Private Tour
Likely to Sell Out 2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
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Florida
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Superb148 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just wind in the sails, salt in the air, and the kind of quiet glide ... More
Private Tour
Likely to Sell Out Suncoast Sailing's Sunset Sailing Experience!
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Florida
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Superb282 reviews4.9
Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually suppos....
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
Likely to Sell Out Sunset Sail Cruise in Key West
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Florida
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Superb295 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour
Key West Sunset Sail Aboard Legendary Schooner Appledore
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More
Private Tour
Likely to Sell Out Key West Sunset Sail Aboard Legendary Schooner Appledore
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Florida
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Superb363 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Private Tour
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
Private Tour
Likely to Sell Out Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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Florida
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Superb1,003 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Private Tour
Fort Lauderdale Sailing Charter
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More
Private Tour
Likely to Sell Out Fort Lauderdale Sailing Charter
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Florida
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Superb404 reviews5
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....
Private Tour