I read 'Sailing For Dummies' in the winter, bought our first boat (a 26' Nash) in the spring and sailed in Georgian Bay all summer without any training or experienced sailor on board. We made a few mistakes but we and the boat survived.
The first winter we took the Power/sail squadron course. The next winter I took the Piloting course. A couple of years later we took the CYA Intermediate cruising course (a live-aboard, practical course).
In retrospect I wish I had taken the CPS (Power/Sail Squadron) basic boating course before I got on the water. Certain information about rules of the road and chart-reading would have come in useful the first summer!
By the time I got to the CYA course - without having an experienced sailor sail with me - I felt very confident in my abilities. I learned a lot during that course and would recommend it to anyone. One thing I learned was that I wasn't doing it totally wrong and that it is very possible to teach yourself how to sail.
Now, if only I could tear myself away from my
boat and start crewing on someone else's in races, I would really be able to fine-tune my skills....