Have you got any actual sailing experience? If not, I would highly recommend you join a sailing club and get some time in on boats. Joining for the weekly around the can races would be a great way to get some experience fairly quickly.
I would also recommend you buy and read Dave Seidman's The Complete Sailor, as it is one of the best sailing primer type books I've seen in a long time. You also should take at least a basic "learn to sail" type course, like the ASA 101, just to give you a basic foundation of skills and knowledge to base your future learning on.
I'd also recommend you read Teresa's blog, Sailing Simplicity
, as she has done much what you're considering, though started at a bit older an age.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.