Nice trip description. I bought a boat out of Crowley's last summer, and sailed it up to Milwaukee. Never sailed on Lake Michigan before. We ended up motoring the whole first day into a small-craft-advisory north wind. I about sh*t my pants when we first got out into the Calumet harbor, and could see spray blasting over the sea-wall.
I am going to try to get up to Door County this summer. I figure on about a 24 hour sail up from Milwaukee.