As the first and only sailing experience in Central Florida, Sailing Orlando is committed to sharing the joy of sailing with our community and its visitors. From day sailing to sunset cruises or sailing lessons, our private sailing experience offers a unique opportunity to sail aboard a 25-foot sloop-rigged sailboat. Guests Become Part of the Crew! A tour with Sailing Orlando is an immersive experience where guests become part of the crew. Whether it’s to help trim the sail or to take the helm, guests have an opportunity to be as involved as much or as little as they want.