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I can recommend a C&C 27 (MK3 - MKV). I sailed it for many years single handed in Florida and recently in San Francisco bay. I spinnaker single handed in 20-30 knots of wind without a problem. Very stable and fast boat, big enough to have some people aboard and small enough to singlehand easily.

Good luck

ps.

I would stay away from a motorboat with sail (macgregor)
 
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