Don't know if it's everyone's cup of tea, but definitely worth trying. If there are any HN'ers in Minneapolis/St Paul, happy to take people out for a try next Spring ;)
I joined the Twin Cities Sailing Club in August, I'm a newb ;), know just enough to be dangerous:
The people in this club are seriously cool people, a great group. Everyone is very generous in terms of teaching less experienced sailors, I've seen nothing but generosity when it comes to tiller time.
I think we have about a dozen boats or so, a mix of scows and daysailers. There are club days twice a week where you can crew up with a skipper and hit the lake. Once you pass your skipper tests, you can take the boats out anytime you please. Annual dues are $200 or so I think.
Oh and we are having our annual banquet November 7th:
http://www.socializr.com/event/830239512/1867039201
If you are not quite ready for putting down $200 and just want to try things out, definitely hit me up in May and I'd be more than happy to take you out!
Which co-op are you a part of? Ever done any ice sailing? ( http://en.wikipedia.org/wiki/Ice_yachting )
There's a pretty strong overlap between (computer) hacking and sailing.