I thought about your "why so expensive" question. There are lots of ways to sail on the cheap, most involve being a member of the "OPBC" (the "Other Peoples' Boat Club"), wherein you make friends with sailboat owners, who usually are looking for crew (betcha a whole lot of them around western Long I. Sound once you get a little experience and start asking around).
Look at the average harbor or marina. Those nice boats sit idle about 95% of the time (and 100% of the time in winter up north). Would you buy a house or car that you used so infrequently? Me, I'd rent or borrow, or go to the gatherings where they need guests (read: crew). There are sailing clubs you can join, or buy a boat with one or two others and share it (takes some cooperation for sure) or join a boat club that has boats you can take out as much or little as you want.
Actually, some well-used but decent coastal cruisers for two can be had for under ten grand. Much of the expense though, is where to keep it, because waterfront property (for docks, marinas, boatyards, yacht clubs) has become so precious that it's more expensive than the boat.
So maybe this doesn't help, but down here (Gulf south) lessons aren't that expensive, the ones I have taught on, whether yacht club adult ed., or private, are (for a group of four per boat/instructor), less than $20 per hour per person. So look around. And don't pass up racing just because you want to learn to cruise. Those owners are *always* looking for reliable crews, and racing is a concentrated course in how to sail in general (though not how to do lots of the cruising/logistics stuff Sailingdog rightly mentioned above). Plus they may even feed you and give you beer ;-)
Last edited by nolatom; 03-02-2008 at 10:18 PM.