Orlando · SAILING

The 5 Sailing Trips in Orlando That Earn Their Price

5 tours  ·  from $72 a head

The good sailing trips fill up while you are still choosing. Below: the 5 to book early, what each includes and how they differ.

Tour of Lakes Escape by Personal Catamaran - Across the open lakes
Cruises & Boat Tours, Orlando Boat Cruises & Pontoon Trips, Orlando Escape Rooms, Sailing, Tour Reviews, Tours

Tour of Lakes Escape by Personal Catamaran

1.Tour of Lakes Escape by Personal Catamaran

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

Take the wheel of a personal catamaran through Clermont’s lakes, cypress waterways, and wetlands on a guided Florida nature tour.

“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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Private 2-Hour Day Sailing Experience - A small sailboat made for conversation
2-Hour Experiences, Cruises & Boat Tours, Orlando Boat Cruises & Pontoon Trips, Private, Sailing, Tour Reviews

Private 2-Hour Day Sailing Experience

2.Private 2-Hour Day Sailing Experience

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

Sail Orlando’s Lake Fairview on a private 2-hour cruise with Captain Dan, hands-on sailing tips, peaceful views, and room to relax.

“What an amazing experience we had. The owner was very engaging. Kept us inform on what he was doing, we even assisted with the sail. We highly recommend this experience. Very friendly and inviting.”

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Private 2-Hour Sunset Sailing Tour on Lake Fairview - What happens during the two-hour sail
2-Hour Experiences, Cruises & Boat Tours, Evening Experiences, Orlando Boat Cruises & Pontoon Trips, Private, Sailing, Tour Reviews, Tours

Private 2-Hour Sunset Sailing Tour on Lake Fairview

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

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

Sail into an Orlando sunset on private Lake Fairview with Captain Dan, a 25-foot boat, room for four adults, snacks, and calm water views.

“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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Orlando: Private Sunset Sailing Trip on Lake Fairview - Setting Sail as the Sun Drops
Cruises & Boat Tours, Evening Experiences, Orlando Boat Cruises & Pontoon Trips, Private, Sailing, Tour Reviews

Orlando: Private Sunset Sailing Trip on Lake Fairview

Orlando: Sailing Tour with Certified Sailing Instructor - What the first minutes aboard are like
Cruises & Boat Tours, Orlando Boat Cruises & Pontoon Trips, Sailing, Tour Reviews, Tours

Orlando: Sailing Tour with Certified Sailing Instructor

5.Sailing Tour with Certified Sailing Instructor

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

Learn to sail on Lake Fairview near Orlando aboard a 25-foot boat, with sunset views, hands-on instruction, drinks, and a small group.

“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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