I'm in the process of teaching myself to sail. I bought Bob Bond's book, The Handbook of Sailing and read it cover to cover. Gave me a good foundation in the various topics. Now I'm studying The Annapolis Book of Seamanship. I've read it completely and watched all the DVD's. I go back and re-read sections as I need them, especially on sail trim, heavy weather sailing, etc.
I've actually gone sailing a grand total of 5 times so far. The first time was a couple months ago, on a Catalina 36, and it was this experience that got me hooked. I bought my boat a month ago and outside of all the work I've been doing (thanks go to Don Casey's Complete Illustrated Sailboat Maintenance Manual) I've taken her out 4 times. The first time was with a friend who sails, in light winds, the rest of the times I've been out by myself....once in strong winds (I consider them strong, 18-25) and worked my butt off! The other times were fun and relaxing, but that strong wind experience really taught me about playing the sails, setting them, and handling puffs. Although I knew what "rounding up" was, until I experienced the boat trying to do it in a strong puff I wasn't ready for.....pucker factor way up there. She never did it as I was quick enough to spill some wind but there was a moment she was heeled way over and trying to turn. Makes you appreciate the gentle 12 knot breezes....
It's absolutely necessary to have a good base of book knowledge and theory (just IMHO) so you know "why" things work and what to do to get you in the ballpark, but getting out there and doing it is what it's all about. I really like going out by myself, because I can experiment without fear of looking like an idiot, and since I have to depend on myself 100% I learn alot every time I go out.
Really, once you have an idea of the basics, it's not that hard. As Penny Whiting says, if it's hard you're doing it wrong.
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1982 Catalina 25 #2897
Eagle Mountain Lake, Texas