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SW Florida Boat Choices/Advice
I have friends who cruise aboard a P365 and they are very pleased with her performance and construction. In fact, I don''t think I have ever met a Pearson owner who was not happy with their boat. I can not say that about many manufacturers.
The Bristol 35 which Jeff mentions would also be a sound choice for your sailing venue. I believe the P365 is a shoal keel while the Bristol is a CB. The CB does give you some performance advantages (which may offset by maintenance issues).
Another vessel at the high end of your price range is the Tartan 37 CB. I have sailed aboard one several times in some fairly challenging conditions and came away thoroughly impressed.