Join Date: Nov 2007
Location: Vero Beach, Florida
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My thoughts are a little different on boat size. I went the route that you are looking at taking and wish that I wouldn't have. My boats with cabins started with A west Wight Potter P-19. It was a fun little boat to sail, but only big enough for two comfortably. Then moved up to a Mac 26S. It was a semi comfortable boat for three, maybe four. but I'm a big guy, and the porta-potty was a pain to use and empty. The rear aft berth was great, like a king size bed. the port berth was a little short for me, but ok for someone under about 5'10". There was no headroom, and ducking and kneeling to cook or do anything wasn't fun. It sailed poorly, and you needed to reef in 15 kt winds or all you would do is round up.
I then bought a fixer upper Hunter 30. It has great headroom and I'm 6'1'' It will hold four comfortably and has a head with a shower and MSD. The Galley is small but works. Ice box, 2 burner alcohol stove, sink, and some storage. I added a grill on the stern rail to keep the heat out of the galley and use it for almost all of the cooking.
It sails great, isn't trailerable, but well worth the comfort. I should have bought the H30 first, but hindsight is 20/20. You can find them from the late 70's or early 80's for around $8k-15k depending on how much work you want to do to it.