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Based on your answers, I'm more convinced than ever that my earlier recommendations (Capri 14.2 or Vanguard Nomad, or similar dinghies) are on target. You'll need to learn about wind and weather, sail trim, currents, basic navigation, anchoring, safety, maintenance, and handling the unexpected. Do that for a while, sell the small boat, and move up to a keel boat. Rinse and repeat as necessary.
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Jim R.
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