I would not hesitate to do it in a well founded cal
20. CAL 20 Sailboat details on sailboatdata.com
Anything with a cabin
, of good build quality, would do.
If you want to be more comfortable, a 26' is about as small as you want to go. Standing headroom
basically changes boat life from "camping" to "inconvenient." When you get up to 30' boats are downright comfortable, but the maintenance
becomes more of a burden.
Anything smaller or lighter than a Cal20 would start to get scary. You want it to be strong, seaworthy
, and safe. These are all easy to achieve in a small boat, but the comfort is just not there, and there is some psychological thing about being in a really small boat that makes you feel unsafe.