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 is UP!
A couple of them I saw were the Brewer Nimble 20 and Rob Roy 23.
http://sailboatdata.com/viewrecord.asp?class_id=5994
http://sailboatdata.com/viewrecord.asp?class_id=4334