The 5 Best Sailing Trips in Orlando

1.Tour of Lakes Escape by Personal Catamaran

★★★★★★★★★★5.0 · 97 reviews · from $95Our pick

Drive your own stable personal catamaran through Clermont’s lakes, marshes, cypress corridors, and narrow waterways. A guide such as Nate or Richard leads the way by two-way radio, sharing local history, wildlife facts, and safety tips. The two-hour tour costs $95 and returns to Cypress Cove Marina.

“Well worth the trip. Our guide was fantastic. I believe she had as much fun as we did. we will be back again and bring more people.”

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2.Private 2-Hour Day Sailing Experience

★★★★★★★★★★5.0 · 46 reviews · 2 hours (approx.) · from $89

Spend two private hours on Lake Fairview aboard a 25-foot keel sailboat with Captain Dan Pollock. You can relax in the cockpit, help with the lines, try the helm, or learn basic sailing skills. The boat holds up to four adults and returns to the Lee Road meeting point.

“Thanks, Captain Dan. We had a great sail with you, and thanks again for the impromptu lesson. We’re really looking forward to continuing to learn to tack and jibe.”

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3.Private 2-Hour Sunset Sailing Tour on Lake Fairview

★★★★★★★★★★5.0 · 34 reviews · 2 hours (approx.)

Join Captain Dan of Sailing Orlando for a private two-hour sunset sail on Lake Fairview. Your group of up to four adults has cockpit seating, a small cabin, cooler space, bottled water, and the chance to bring food, drinks, and music for a relaxed evening away from Orlando’s theme-park crowds.

“I tried to upload some amazing photos of the sun setting but it wouldn't allow me. You do not want to miss this. It was such a relaxing and beautiful experience! The ambiance was nice and the captain made sure we were comfortable and felt safe. So romantic and lovely!”

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4.Private Sunset Sailing Trip on Lake Fairview

★★★★★★★★★★5.0 · 10 reviews · from $89

Spend two private hours on Lake Fairview with Captain Dan, a USCG-licensed sailing instructor. Help steer, trim the sails, or simply watch the sunset from a 25-foot MacGregor sailboat. Bring your own snacks, drinks, and music for a relaxed Orlando date night or small family outing.

“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!”

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5.Sailing Tour with Certified Sailing Instructor

★★★★★★★★★★5.0 · 4 reviews · 2 hours · from $72Best value

Join captain and sailing instructor Dan for a two-hour cruise on Lake Fairview aboard a 25-foot MacGregor sailboat. Help raise sails, trim lines, steer, and enjoy a Florida sunset. The group is limited to five, and you may bring snacks and drinks, including alcohol.

“I had a wonderful time. I took this adventure with my 80-year-old mom, celebrating my birthday. This sailing trip was her first sailing experience. Our host, Dan, was personable and helpful, making the experience an incredible moment for both of us. The trip was calm and added to end a fantastic birthday weekend.”

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