Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 128 Sailing Trips activities in Florida. Sort by Popularity. - Page 2Classic 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
-
Florida
-
Superb241 reviews4.9
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, compl....
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
-
Florida
-
Superb468 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 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
-
Florida
-
Superb893 reviews4.9
Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in....
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
-
Florida
-
Superb199 reviews4.6
Our afternoon dolphin watch is limited to an intimate number of passengers to optimize your views! E....
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
-
Florida
-
Superb254 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wil....
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
-
Florida
-
Superb328 reviews4.7
From the Pier to Paradise. You’ll sail by the beautiful shorelines of St. Pete, pass under the stu....
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)
-
Florida
-
Superb1,517 reviews4.9
Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure ....
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
-
Florida
-
Superb461 reviews4.9
This tour is an intimate experience, our groups are 3-5 people per boat maximum. We have two boats. ....
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
Likely to Sell Out Key West: Sunset Sail + Reef Snorkel & Sandbar
-
Florida
-
Superb35 reviews5
Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. Wh....
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
-
Florida
-
Superb732 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 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
-
Florida
-
Superb109 reviews4.9
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics,....
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More
Likely to Sell Out Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
-
Florida
-
Superb61 reviews4.9
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....
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
-
Florida
-
Superb988 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
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
-
Florida
-
Superb592 reviews4.7
Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of t....
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
-
Florida
-
Superb184 reviews4.9
Create memories that lasts a lifetime with a day on the Gulf of Mexico sailing to a private island f....
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
-
Florida
-
Superb194 reviews4.9
Experience the Magic of Cocoa Beach with Our Dolphin Adventure Sail! Join Cocoa Beach Catamaran for....
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
-
Florida
-
Superb43 reviews5
Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get so....
Likely to Sell Out
Sandbar, Snorkel, and Sunset Sail in Key West
This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon: extended time at a shallow-water sandbar, snorkeling in clear backcountry waters, and a sunset on the water. Sailing aboard a hi... More
Free Cancellation
(Saving 10% )
Likely to Sell Out Sandbar, Snorkel, and Sunset Sail in Key West
-
Florida
-
Exellent6 reviews4.2
This trip combines three of the most sought-after experiences in Key West into one relaxed afternoon....
Free Cancellation
(Saving 10% )
Likely to Sell Out
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
Free Cancellation
(Saving inf% )
Likely to Sell Out Sail & Splash Excursion in Ft. Lauderdale
-
Florida
-
Superb278 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
Free Cancellation
(Saving inf% )
Likely to Sell Out
3 Hours Ultimate Watersports Excursion in Miami
All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable and stable Catamaran for an unforgettable all-inclusive water experience. Highlights: - Extreme Watersports: Feel the thrill wi... More
Free Cancellation
(Saving inf% )
Likely to Sell Out 3 Hours Ultimate Watersports Excursion in Miami
-
Florida
-
Superb278 reviews4.8
All-Inclusive Catamaran Adventure in Miami: 3 Hours of Adrenaline and Party! Board your comfortable....
Free Cancellation
(Saving inf% )