Doc, you can start in macinaw, and stop at the following beautiful michigan ports heading south and end up in my town of Holland and leave your boat
there is Petosky, Harbor Springs, Charlevoix, Pentwater, Whitehall, Muskegon, Grandhaven, and then Holland. 7 more miles and hit Saugatuck, 15 more and hit South Haven. all resorty port towns with nice waterfronts, restaurants, shops, and beautiful public beaches.
many ports to enjoy your boat and the beautiful sand dune scenery along the michigan coast.
some formula owners are thinking of a formula rendevou at the June smoke on the water poker run in Grand Haven. I know of a 302 and 41' formula both with kaamas considering the trip from Chicago.