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Sailed a lot growing up weekending on El Gato, a Cal 25 (sails ersatzly for blankets & bedsheets in the bow) and later club racing a Ranger 26 named Witchcraft as sole crew for my dad (and winning too often for the non-blue-collar guys to the point that they paid him off to sandbag a little).
Considering buying La Teresa, pictured, a gorgeous green Sabre 30 Mark I ($9k obo, on the hard) for like a couple thousand bucks to live aboard and go semi-permanently cruising down to the 'ribb maybe.