The trip you are thinking of is a lot of fun. From Waukegan I migt suggest a stops in Racine, Milwaukee, Port Washinton, Sheboygan, Manitoc, Kewaunee, (skip Algoma, too shallow) Sturgeon Bay. If you want to venture farther north (well worth it if you have the time) It will take you the better part of a day to get from Sturgeon Bay to Egg Harbor depending on weather. The transit from Sturgeon Bay out into Green Bay can be time consuming.
My home port is Egg Harbor. I would be happy to answer any questions you may have.
Maxum 3200 Miss Adventure
Formerly - Tartan 34C Yawl