Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 128 Sailing Trips activities in Florida. Sort by Popularity.Miami Millionaires Sightseeing Cruise
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmerizing beauty of Biscayne Bay, while getting an exclusive glimpse into the luxurious lifestyle of Miami's elite, with a bilingual com... More
Likely to Sell Out Miami Millionaires Sightseeing Cruise
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Florida
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Exellent1,418 reviews4.3
Join a sightseeing boat tour of Miami Beach and the iconic Millionaire's homes. Explore the mesmeriz....
Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on one of Sebago's modern sailing catamarans while sipping sparkling wine or your favorite cocktail and fea... More
Likely to Sell Out Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres
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Florida
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Superb3,518 reviews4.7
Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic me....
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand K... More
Likely to Sell Out Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
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Florida
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Superb789 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy ... More
Likely to Sell Out Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
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Florida
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Superb1,352 reviews4.9
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t ....
Key West's Favorite Afternoon Dolphin Sail
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! Enjoy sailing aboard a 60' catamaran to the dolphin playground to view wild dolphins play and frolic in their natural habitat. Atla... More
Likely to Sell Out Key West's Favorite Afternoon Dolphin Sail
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Florida
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Superb126 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
Key West Reef Morning Snorkeling with Breakfast and Mimosas
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light Breakfast and sail to the Key West living reef where you will see coral and tropical fish. All snorkeling... More
Likely to Sell Out Key West Reef Morning Snorkeling with Breakfast and Mimosas
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Florida
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Exellent579 reviews4.5
Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip....
Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 2.5 hour sail is more like a private cruise than a group tour and is one of the top things ... More
Likely to Sell Out Key West Sunset Sail: Dolphin Watching, Wine, and Tapas
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Florida
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Superb693 reviews4.6
Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to ....
Sunset Sail in Key West with Beverages Included
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise is legendary. Being out on the... More
Likely to Sell Out Sunset Sail in Key West with Beverages Included
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Florida
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Superb901 reviews4.9
Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champa....
St. Augustine Live Music Cruise with Drinks and Sunset Option
**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** Sailing Catamaran tours will resume on March 2nd. Come aboard our spacious state-of-the-art catamaran on St. Augustine's only all ... More
Likely to Sell Out St. Augustine Live Music Cruise with Drinks and Sunset Option
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Florida
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Superb312 reviews4.8
**45' Corinthian Power Catamaran will be operating this tour from January 13th - March 1st 2026.** S....
Key West Afternoon Reef Snorkeling with Open Bar
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start a sail to the Key West living reef where you will see coral and tropical fish. All snorkeling equipment is provided an... More
Likely to Sell Out Key West Afternoon Reef Snorkeling with Open Bar
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Florida
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Exellent417 reviews4.5
Dip and Sip Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip w....
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
Likely to Sell Out Key West Sunset Sail Aboard Legendary Schooner Appledore
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Florida
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Superb239 reviews5
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th cen....
Likely to Sell Out Key West Dolphin and Snorkel Experience
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Florida
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Exellent332 reviews4.4
The Sunset Watersports Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key....
St Augustine Nights of Lights Tour with Live Music and Sunset Opt
Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday magic from the water, giving guests sweeping, unobstructed views of the illuminated bayfront, the Bridge of Lions, and Castillo de... More
Likely to Sell Out St Augustine Nights of Lights Tour with Live Music and Sunset Opt
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Florida
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Superb69 reviews4.7
Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday ....
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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Superb439 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
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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Superb586 reviews4.7
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....
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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Superb469 reviews4.9
SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft....
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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Superb540 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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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Superb252 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
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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Superb948 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Panama City Beach Sunset Sail on 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 Panama City Beach Sunset Sail on The Footloose Catamaran
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Florida
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Superb441 reviews4.8
If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset S....