I've had the privilege of sailing on some wooden classics. As a kid on a Concordia sailing down Maine's Eggemoggin Reach. College days, Buzzard's Bay in a full southwesterly by myself in a 1907 Heresoff 12 1/2. (What sweet little boat! So easy to sail upwind in the full 25 knots of wind and short steep chop.) Years later I raced those same waters on a competitive IOR boat. Watched the 1930s Herresoff S-Boats sail away from our fleet upwind like we were dragging anchors. (The race committee sent them to a different mark to not rub it in. They knew!) I saw and laughed to myself. Of course, I've known there were fast old boats along time. Grew racing around Star boats. In light air upwind, those 1913 boats made the 1970s handicap racers look like dogs. So did our local Manchester I boats from the '30s. Never got to sail on the old fresh water rocket - the E-scow.
I wound never have the patience even if I had the money for a traditional wooden boat. Now a much lighter wood/epoxy boat? That would be fun! But I 'd have to live somewhere else where was either big water or really interesting water.
Ben.