Sailing Trips in Florida
Top 10 Best Florida Sailing Trips
Found 115 Sailing Trips activities in Florida. Sort by Popularity. - Page 6Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats
Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More
Private Tour
Private Reef Snorkel and Sail Trip
Key West is surrounded by stunning reefs. Tell us what you’d love to see and we’ll create the perfect snorkel adventure, complete with cold beer, wine and soft drinks and healthy snacks. If you’ve been looking for the ultima... More
Private Tour
Tiki Pub Eco Adventure in Fort Myers Beach
This 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 our p... More
Private Tour
Sail Around Key West on the 46-Foot Catamaran
This day typically lasts about eight hours (or can be 4) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the ... More
Private Tour
Learn to Sail in a Bonafide Racing Vessel in Biscayne Bay
This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More
Private Tour
Private Charter 6 Passenger Sandbar, Snorkel, Dolphins
Cowfish offers a smooth and comfortable ride, versatility, and ample space for 6 or fewer in a small package. Whether you want to lounge on the sandbar, snorkel at your own pace, or enjoy dolphin watching, Cowfish provides a great... More
Private Tour
Nights of Lights Sailboat Tour St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More
Private Tour
Key West Wreckers Race Aboard Schooner America 2.0
Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More
Private Tour
Private 2-Hour Wind and Wine Sunset Sail in Key West
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There... More
Private Tour
Private Afternoon Snorkel with Sunset Sail in Key West
Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More
Private Tour
Bimini Charters - Private 6 Hour catamaran sail & snorkel
We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of time to determine your goals for the day and make them happen. Our guests almost always say that their trip with us was the highlight... More
Private Tour
Introduction to Power Boating
Take the helm of a power boat and unlock the thrill of mastering the waves with our immersive Introduction to Powerboating class! Dive into hands-on learning tailored for beginners, igniting your passion for navigating power-drive... More
Private Tour
Sail the waters of Key West on Bella Maggio Yacht
This day typically lasts about four hours (or can be 8) from the time you leave Marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the ocean... More
Private Tour
Sunset Luxurious Charter Aboard Atlanta in Key West
This day typically lasts about four hours (or can be 8) from the time you leave the marina to the time you get back and may include fueling time. There is no chance to forget anything as you will go out on the same yacht for the o... More
Private Tour
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
Private Tour