Re: Michigan Summer Itinerary advise?
We spent a night in Grand Haven a few years ago. Not 20 yards in front of our transient slip (35' slip) was a frozen custard shop. The evening light & water show is NOT all it's advertised to be. But, if you're there, you might as well check it out.
There are plenty of restaurants and a few streets to walk in South Haven. Of course, you can walk out to the end of the pier too.
Grand Haven is a bigger South Haven--and you get custard. It's like a mini boardwalk.
Saugatuck is so much fun getting into--sail up the river and into town. I'm used to sailing up a channel and that's about it--Michigan City, New Buffalo, St. Joe (although St. Joe has a bit of a river too we don't go that far). Talk to the locals and they will tell you the secrets for staying into the deep water. We saw 0.0 feet of depth on the way across the small lake to the marina. But, we didn't touch. Things are deeper now.
All of the harbors you mention are fun. It's a little far, but think about St. Joe too. Nice pier, cool drawbridge, etc.
Your timing sounds GREAT, and allows for plenty of wiggle room. We did one trip like this:
Day 1: Leave Waukegan evening.
Day 2: Arrive Grand Haven morning. Catch up on sleep midday. Go out to dinner. See light show. Good night sleep
Day 3: Leisurely sail to Saugatuck. Arrive, dinner, sleep.
Day 4: Leisurely sail to South Haven. Repeat day 3.
Day 5: Depart South Haven early. BIG long day back to Waukegan.
We had several extra days available--those much more experienced than I suggest one day in harbor for weather issues for every one day sailing.
You note that we don't linger in the harbor towns much. They're beautiful, but we enjoy being on the lake and working the boat. The destinations, for me at least, are an excuse to SAIL!