Don''t have a Cal 39 myself, but a fellow member of our club does, for what seems like the same reasons as you. The boat is big enough to be comfortable but small enough to be handled without a lot of crew. The construction seems relatively solid, though like the guy who went around the world in a Cal 2-30, you might want to beef it up in a few places. My friend races occasionally, and the boat performs decently, though I razz him about the refridgerator, freezer, watermaker,
radar and genset slowing him down. He and his wife enjoy cruising their boat up the New England coast, and it gets them where they want to go.