I can't recall off the top of my head the NM's between the ports you have listed. I would sugesst that you try and keep it around 50NM's per day.
Waukegan - Milwaukee might be right around there.
There are several nice marinas/harbors not on your list that might break it up into shorter legs.
Kenosha, Racine, Port Washington, Manitowoc, Two rivers, Kewaunee, and Algoma.
Note: I just checked your milage between ports and it looks like a sound plan other than the leg between Sheboygan to Sturgeon.
That is about 71NM's. Certainly doable, but it would depend on your confidence level. You might want to add another stop or two to break it up.
Take your time, don't be in a hurry, thats what cruising is all about, enjoy the ride.
Courtney is My Hero
If a man is to be obsessed by something, I suppose a boat is as good as anything, perhaps a bit better than most - E.B. White