Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 108 Sailing Trips activities in Florida. Sort by Popularity. - Page 2Key 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
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Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast
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Florida
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Superb35 reviews4.7
Embark on an adventure off the shores of Key West, where the turquiose waters of the Gulf of Mexico ....
Free Cancellation
(Saving 20% )
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
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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Superb147 reviews5
Experience a Magical Sunset in Cocoa Beach! Set sail into the golden hour and enjoy a stunning eveni....
Private Tour
Private Guided Sunset and Dolphin Cruise up to 6 Passengers
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a cooler with bottled water a... More
Private Tour

Private Guided Sunset and Dolphin Cruise up to 6 Passengers
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Florida
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Superb66 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
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
Private Tour

Key West Reef Snorkel & Sail Adventure
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Florida
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Superb518 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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

Dolphin Adventure Sail in Cocoa Beach
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Florida
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Superb145 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
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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Superb267 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
Private Tour
Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins, or watch the sunset from classic Destin Locations Crab Island and Norriego Point. Our boat includes a full restroom, as well as a... More
Private Tour

Private Sunset and Dolphin Cruise in Destin-Up to 16 Guests
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Florida
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Superb38 reviews5
Our cruise is a private tour to see Destin's sunset as you want to see it. We can look for Dolphins,....
Private Tour
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
Private Tour

Suncoast Sailing's Sunset Sailing Experience!
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Florida
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Superb225 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private Tour
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
Private Tour

Sunset Sail in Miami: Complimentary Champagne Toast
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Florida
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Superb225 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
Private Tour
Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More
Private Tour

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
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Florida
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Superb29 reviews5
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....
Private Tour
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
Private Tour

Catamaran Day Sail Shelling Excursion 42ft. Mainecat Cool Beans
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Florida
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Superb142 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
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

Southwest Florida Sunset Sail
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Florida
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Superb437 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
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

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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Florida
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Superb902 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Private Tour
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
Private Tour

4-Hour St. Pete Pier to Egmont Key Experience by Ferry
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Florida
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Superb292 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
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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Superb1,433 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
Private Tour
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
Private Tour

Key West Sailing & Snorkeling: A Reef Adventure
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Florida
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Superb143 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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
Sail Biscayne Bay: An Intimate Eco-Adventure
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
Private Tour

Sail Biscayne Bay: An Intimate Eco-Adventure
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Florida
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Superb422 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
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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Superb233 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....
Private Tour