I met a true sailor the other day while looking at boats. Walking down Haight Street you wouldn't notice this guy, he would blend in so nicely. You certainly wouldn't expect to see him at the St. Francis Yacht Club. And you also wouldn't expect to see him sailing a Catalina 27....which is probably why he's selling it to get a Folkboat. Much much more appropriate for this Gentleman.
Anyway, I have a habit of researching so I looked over this guy's website and found this tremendous story about his sail from Berkeley to Mexico. The only questionable decision he made was to sail without an engine, but it's pretty apparent that he's a good enough sailor to pull it off.
Well, wait a second, this may have been a bit questionable:
"I was boarded by the coastguard just outside of Newport. They were actually very friendly, very respectful, and almost seemed embarrassed by the way they were intruding in my space. They were all-around nice guys. At one point one of the coastguard guys pointed up and asked "What's the black flag for?" I paused for a second and then suddenly yelled "Anarchy!!" He jumped in his seat, then nodded and went back to his clipboard."
Anarchy on the open seas, I love it.