That should be great fun! There are groups of old guys doing so in 20-24' simple boats. I ran into a few doing so up here in the PNW. They had been all over PNW US/Canada in their little ships. Simple and easy. Heck, you're just sleeping inside really. The rest of the time dining out , cooking
breakfast in the cockpit
or having a beer
at some local haunt! What could be better? Your 2-4 hp outboard
fails? Screw it, buy another! One pull and the mainsail
A couple of them I saw were the Brewer Nimble 20 and Rob Roy 23.