My first time ever sailing was 3 weeks ago on my newly purchased Columbia 28. I read tons of books from Nigel Calder to Tania Abei. I even played "sailing simulators" online. I've been out a half dozen times in the 3 weeks and have had a ball! Now for the caveat...I can tack and sail half decent on most points of sail (except a run) but there's always a nagging feeling that I could be doing something wrong or doing better. "Is that the way the sail should look at this point?" or "Should I tighten the mainsheet?". There's always a doubt.
I DO NOT regret getting out there and doing it on my own but on the same token, I fully intend to get some sort of formal or informal training. It just seems to me that having the knowledge that I'm not just doing something right, but doing it well would add greatly to my enjoyment.
I intend to do some extensive coastal cruises next year so I have plenty of time to learn. I have even talked to a couple of experienced sailors on the dock and all have volunteered their time to go out and sail with me. To me, that's the key (learning on my own boat). I know my tired old mainsail will look different from the new Hunter 25 two slips down or the boats at the local school.
Just my rambling thoughts on the subject. If all else fails, just go out and DO IT!
1970 Columbia 28