I will always regret bringing my boat from Maine to Miami on a truck.
I think the Wasque 26, Dyer 29 or any of those small Yankee single engine boats would be a good choice. I'm partial to the Ellis 28.
They have a turn of speed when you want it but are economical if you go slow. In that size boat your going to have a V-berth to sleep in. A basic galley and probably a combination head / shower. I can live like that for a week or so at a time, then I want a hotel room and nice restaurant. Shouldn't be a problem on the East coast.
I think the boat must have a flying bridge. (That's just to stir up Mark.)