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Orlando Sailing trips & boat tours

Our most recommended Orlando Sailing trips & boat tours

Orlando: Private Sunset Sailing Trip on Lake Fairview

1. Orlando: Private Sunset Sailing Trip on Lake Fairview

Set sail on a private boat tour of Lake Fairview. Admire the sunset as you learn how to sail. Meet your tour guide and sailing instructor at the boat ramp. Put on your life jacket then, climb about the 25ft vessel and set sail. Be as involved as you like, learn the fundamental principles of sailing or sit back and relax on a sunset cruise. Enjoy an immersive experience and become part of the crew. Help trim the sail and take the helm. Follow your instructor's commands to raise and lower the sails, steer, and turn the boat. Then, relax in the comfortable cockpit as you admire the sunset reflected in the water.

From Orlando: Clearwater Beach Pirate Cruise with Lunch

2. From Orlando: Clearwater Beach Pirate Cruise with Lunch

Start the day with pickup from Orlando in a luxury vehicle, then head towards Clearwater Beach. Hop onboard the Pirate’s Ransom and greet your friendly crew. Learn how Florida was a well-known pirate hangout in the 17th and 18th centuries, and hear stories of Captain Kidd and the infamous Blackbeard. Set sail onto the glistening waters of the Gulf of Mexico and lookout for dolphins swimming in their natural habitat. As you cruise, enjoy 2 hours of family fun including a treasure hunt, face painting, water guns, story-telling, and dancing. During the day, enjoy free time to sunbathe on the white sands of Clearwater Beach or go for a swim. A tasty lunch at a local beachside restaurant is included. At the end of a truly epic adventure, relax on the return journey to Orlando.

Orlando: Sailing Tour with Certified Sailing Instructor

3. Orlando: Sailing Tour with Certified Sailing Instructor

Set out on a 2-Hour sailing experience in Central Florida. Learn how to sail with a certified sailing instructor, and enjoy drinks and snacks along the way. Meet your tour guide and sailing instructor at the boat ramp. Put on your life jacket and climb aboard the 25-foot MacGregor sailboat. Be as involved as you like — learn the fundamentals of sailing or sit back and relax on a sunset cruise. Enjoy an immersive experience and become part of the crew. Help trim the sail and take the helm. Follow your instructor's commands to raise and lower the sails, steer, and turn the boat.

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What people are saying about Orlando

Overall rating

4.2 / 5

based on 14 reviews

The pirate cruise was excellent. Both the children and the adults alike had a blast! Crew members were very interactive, and accommodating. For the price, you can’t beat; transportation to and from Clearwater, a free meal at Crabby’s dockside (in which I would recommend that you eat there, even if the meal wasn’t free), free soda, beer, and wine. Brad the driver from Florida real guides was fantastic, attentive, and very accommodating. Brad explained everything, helped everyone check in, made rest stops, and represented Florida real guides professionally. As with anything you do in life, if you want to have fun, you will have fun…..so please participate…….arrgh!

Dan was a great host and answered all of our sailing questions, we learned how the boat works and helped steer and raise/lower the sail! Dan was very communicative before the experience and monitored the weather conditions, he reached out and personally rescheduled my excursion when my original date got rained out. The lake was beautiful and we passed a variety of other boaters while out on the water—–highly recommend this trip for locals and tourists!

Everyone was very nice. The driver and your guide ensured nobody was left behind, they patiently waited for those who were tutelage. Lots of fun activities for the kids on the pirate cruise and nice crew staff.

Dan is an experienced sailor. And he made our experience a wonderful one. I highly recommend booking him!

It was awesome! He was so personable and a great guide!! I would definitely go again