I agree, the club is probably the best way to go. While cost is close to slip fee price there is no maint/improvemnt costs, insurance, rego, etc... that go along. Some clubs do offer cruising memberships that allow overnighting/extended cruising. Don't get hung-up on the "all lines lead to cockpit" thing. Much better to learn what they do the old school way before worrying about things like that. (What if something breaks and you HAVE to go to the mast?)
Try J World in Annapolis. I think they offer both daysailing and cruising and you should be able to crew for Wed. races some if you are interested. However, if your current screen name is correct you may have some issues getting accepted to many clubs.
