Caleb,

Another sailing option that I have found when visiting my in-laws is to go out with a guy named Chris Pliska. He sails an Prindle 18-2 and you can sign up to go out with him at the local beach shop that is call Kailua Sailboards and Kayaks. It is about $100 for 2 hours, so not cheap, but I much prefer it to going out on a large boat. And he is happy to let you skipper once he is comfortable that you know how to sail.

Drew