Join Date: May 2006
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I don't know Chi-town to well, but a friend of ours just took a small boat sailing class there. If you can get your feet wet (no pun) in flying juniors, lazers, flying scots, melges, J-24's, whatever, those skills and terminology will all transfer. Also, getting a little time in small boats will give you that "experience" to get into bigger boat racing. It might cost a few bucks, but check around in the phone book/internet for a short small boat sailing/racing class for beginners. If all else fails, call one of the yacht clubs (like CYC) and ask them. I'm sure they'll point you in the right direction.
I'm over here in South Haven on the other side of the lake. If you were closer, you'd be welcome to come out with us sometime. I'm in the process of teaching my girlfriend to sail :-).