Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 130 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
Key West Sailing & Snorkeling: A Reef Adventure
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Florida
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Superb189 reviews4.8
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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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Superb94 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
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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Superb167 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
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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Superb543 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
Likely to Sell Out
Key West Dolphin and Snorkel Experience
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key West Sunset all in one trip.... More
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Likely to Sell Out Key West Dolphin and Snorkel Experience
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Florida
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Exellent338 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
Free Cancellation
(Saving 10% )
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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Superb447 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
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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Exellent373 reviews4.4
Fury’s Snorkel Adventure is unique for its combination of thrilling snorkeling and a vibrant saili....
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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Superb234 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
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
Likely to Sell Out Suncoast Sailing's Sunset Sailing Experience!
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Florida
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Superb261 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
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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Superb222 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More
Likely to Sell Out Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak
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Florida
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Superb95 reviews4.9
Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authent....
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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Superb693 reviews4.8
A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the br....
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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Superb711 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....
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
Likely to Sell Out Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
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Florida
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Superb32 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
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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Superb444 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 Champagne Sunset Catamaran Cruise
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy included wine, sparkling wine, beer, sangria or margaritas on board the boat. . As you sail thr... More
Likely to Sell Out Key West Champagne Sunset Catamaran Cruise
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Florida
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Superb587 reviews4.7
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....
4-Hour St. Pete Pier to Egmont Key Experience by Ferry
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stunning Sunshine Skyway bridge and perhaps see a dolphin or two! This is the only charter offering service from downtown St. Petersb... More
Likely to Sell Out 4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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Florida
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Superb309 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
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
Likely to Sell Out Bimini or Grand Bahama Island by Ferry
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Florida
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Good17 reviews3.4
Escape to the Bahamas! Get ready for an unforgettable day in the Bahamas, just off the coast of Flor....
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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Exellent86 reviews4.5
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
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. *Parti... More
Likely to Sell Out Sunset Sailing Cruise Aboard Schooner Clearwater-Clearwater Beach
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Florida
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Superb230 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....