Hi Matt: I am a sailor, (and a pilot) Sailing is not difficult but does take some skill to handle the boat, know the wind, learn the rigging, knots etc, and you must learn navigation and weather patterns. There are many "how to" books available, that is a good place to start. I sail mostly on lake Michigan but lost my boat a few years back. (Got knocked down in a storm 20miles out and sank) I am searching for a replacement now. Sailing is a great adventure and it does not eat you alive in gas and insurance. The U.S. Power Squadron has a good 6-8 week class which includes navigation, weather, waterway rules, etc . Good luck and I would be glad to answer any questions you come up with. Ted J>