Free and not-so-free boating instruction for a would-be sailor
Here's something I posted on a bulletin board in response to a would-be sailor...
Welcome and keep turning those dreams into reality. I hope you'll hook up with a sailing club, co-op, or one of the more water-oriented/less stuffy yacht clubs so you can hang out with sailors. Volunteering to help out with regattas and sailing events is also a good way to get closer to boats. Most states and organizations such as the USCG Aux and US Power Squadrons also offer inexpensive or free basic safety classes.
A good homework assignment for you this winter is to think about the kind of sailing you'd like to do, your general likes and dislikes and strengths and weaknesses, and how that might translate into a boat. Of course, there is no one perfect boat -- except maybe the "next one". And, crewing on other people's boats (OPB) is also a wonderful thing.
free is good, but limited in what it can do
The free classes are good and worth doing, but they don't replace the regular sailing classes. Typically the free or almost-free classes are offered by a state agency and are indoor-only classroom meetings for a day or a couple of evenings. They are generally not specific to sailboats, but cover general boating terms, equipment requirements/laws, an introduction to the navigation rules/rules of the road, navigation lights, whistle/horn signals, buoys and navigation aids, nautical charts, boat trailering and launching, common hazards and emergencies, skipper responsibilities, etc. All of this is extremely worthwhile, but it won't turn you into a skilled sailor on the water. For that, you'll need some form of practice and maybe coaching.
Somewhat more extensive, with a moderate fee, are the US CG Auxiliary and Power Squadron courses; these may meet for quite a few evenings. These are mostly not sailing-specific but do go into a good lot of detail.
If you find a good skipper to crew for, that can take the place of a whole lot of classes. And after crewing with a few skippers, you may get an idea of what a good or bad skipper is!
Most expensive of course are the classes offered by commercial sailing schools. They have the advantage of being hands-on and on the water and being focused on turning students into sailors. They also have only a few students per instructor, so you get plenty of individual attention.
One good thing about doing the "book learning" stuff before taking a commercial on-the-water sailing class is that you can then focus more on the boat handling and sail trimming parts of the class, where you can get the most value out of the instructor as your sailing coach and helping you learn the stuff you can't get out of books.
Once you've got the basics of sailing, joining a club, community sailing center, or co-op or getting a small boat would be some good ways of getting time on the water that's not too expensive. Even a tiny boat is really great for learning the basics. (Little boats have a habit of immediately getting you wet or embarrassed if you make a big enough mistake.)
To me, the best approach seems to be a mix of finding every way you can to get time on the water, meet other sailors and crew for different skippers, as well as learn the theory from books, videos, and the internet.