My husband and I did the Sunset Sail with Captain Guy and his crew (Elan and Emily). It was awesome. We would highly recommend it to anyone. And it was very reasonably priced-- the organization is actually a not-for-profit and the tourist sailing trips help fund ecological education programs that they provided to school children.
We showed up at Salty Sam's Marina a little after 4 pm. Captain Guy and his crew provided great hors d'oeuvres from the restaurant located on the dock, and we picked up some drinks at the shop on the dock to take on board with us. This is the ship's first year in Fort Myers (it comes from Michigan and the Great Lakes), so they are still building up business. As a result, we were the only people on the 65' sailboat! They were kind enough to take us out anyway and we had a fabulous time on our private cruise. They taught us some basic stuff about sailing and the lets us help with the sails. We saw four dolphins out playing and a gorgeous sunset. The whole trip took about two hours and it was enjoyable the whole time.
Our one recommendation: Make sure to bring sweatshirts and coats, because it gets chilly after the sun goes down!