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Richard is spot on. Learn in protected waters on a dingy, like the suggestions I tossed out. Then learn to sail local waters (bays) in a small keelboat or swing-keel boat. Coastal cruising will require a reasonable level of experience and probably a 26-35 foot keelboat. I did some coastal cruising in 28' and 38' keelboats. I did lake/bay/close-offshore racing in a J/22.
Buy used as you move up the size ladder so you can sell them at / near break even. Take some of the classes offered by sailing organizations such as the American Sailing Association or US Sailing.
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Jim R.
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