The other day someone told me it was impossible to cruise comfortably on a boat less than 30 feet or less. Well, all I can say is, I'm sure it might be impossible for him but not for me.
For instance, we lived and cruised full time on our first Loose Moose 25'6" with a 7'6" beam) for four years in Europe...
As it happens the Jessie Cooper design by Phil Bolger still falls into the favorite boat I've owned slot for a variety of reasons.
But, yeah you can live and cruise on a 26-foot boat without giving up comfort or safety as long as you're sensible.
So, it is doable.
Here's another design I wouldn't mind cruising in the same size bracket the L' ETROIT MOUSQUETAIRE by Gilles Montaubin which packs an incredible amount of comfortable living and storage space into a 25' 11" X 8' 4" Envelope.
I won't even begin to get into the large number of classic plastic production boats except to say there is a plethora of excellent boats in the sub 30-foot range going for stupidly cheap prices.