Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 137 Sailing Trips activities in Florida. Sort by Popularity. - Page 2Key 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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Superb209 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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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Superb238 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wil....
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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Exellent93 reviews4.5
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
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
Likely to Sell Out Sunset Dolphin Sail Aboard the Footloose Catamaran
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Florida
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Superb463 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
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
Likely to Sell Out Sail & Splash Excursion in Ft. Lauderdale
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Florida
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Superb274 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
Sunset 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
Likely to Sell Out Sunset Dolphin Sail Aboard the Privateer Catamaran
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Florida
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Superb722 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 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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Exellent378 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
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
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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Superb104 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
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
Likely to Sell Out Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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Florida
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Superb978 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
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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Superb551 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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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Superb1,508 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
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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Superb230 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
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
Likely to Sell Out Suncoast Sailing's Sunset Sailing Experience!
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Florida
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Superb268 reviews4.9
Step aboard Suncoast Horizon, a real working schooner and experience what sailing is actually suppos....
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
Likely to Sell Out Sunset Sail Cruise in Key West
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Florida
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Superb276 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
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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Superb128 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
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
Likely to Sell Out Sunset Sail in Miami: Complimentary Champagne Toast
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Florida
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Superb240 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
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
Likely to Sell Out Southwest Florida Sunset Sail
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Florida
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Superb495 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island for some swimming and shelling (weather permitting) while taking in the sun and spectacular views. Our beautifully, well appointed ... More
Likely to Sell Out Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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Florida
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Superb179 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
Private Boat - Snorkeling, Star Island & Dolphin Spotting
Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k reviews. Connect your phone & be your own DJ—bring your own food, drinks & alcohol. Our boat is fully equipped with a Bluetooth sound... More
Private Tour
Likely to Sell Out Private Boat - Snorkeling, Star Island & Dolphin Spotting
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Florida
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Exellent61 reviews4.5
Step aboard one of the top-rated boat tours in Miami, rated 4.9 stars on Google with over 1.2k revie....
Private Tour
Key West Historic Schooner When And If Sunset Cruise
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More
Private Tour
Likely to Sell Out Key West Historic Schooner When And If Sunset Cruise
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Florida
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Superb132 reviews4.8
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner....
Private Tour