re: Anyone here sail?

But seriously, I'd recommend a small boat first. You learn to sail a dinghy well and you have the basics for most any boat down. Or a catamaran for a summer. It will beat your arse, and you stay wet but holy crap is it ever fun.

But if you want something you can drop into practically any body of water just go find a sunfish or something. You'll knock it over a few times. Get smacked in the head a few times. But you can have a lot of fun on a little boat like that.

I'd recommend a year of that, plus crewing on boats racing if you can find one that doesn't have an a-hole yelling at you constantly, and you'll be in much better shape to decide about a keelboat.