Hi Kesslerbk!
Greenlake's analysis is spot-on - those waters are quite doable in a Daysailer, but be well-prepared. I've never been there, but have sailed Maine in small boats, so some similar considerations. The water is COLD. And the weather is highly changeable and can also be quite cold, even in summer. Have a plan for dealing with hypothermia. The Watertribe folks (of Everglades Challenge fame) have thought out quite a bit of what it takes to adventure in an open boat, check out here to begin with:
https://watertribe.com/Magazine/Y2002/M12/SteveIsaacWhenGodsPlay.aspxBefore venturing any further than Jackson Harbor (itself apparently quite lovely), I'd be asking myself questions like "How do I handle a 3-day blow when I'm stuck on the Michigan side?" or "How will I sleep aboard if the land is marked private, no trespassing?", "Am I ready to handle a breaking wave coming into the cockpit?", and even simply "How will I handle a night of hard driving rain?" All this is doable and has been handled in a Daysailer (and in open dinghies in general), but crossing over to Garden Peninsula is definitely something you'd only want to do after plenty of experience cruising around on the Door County Bayside first.
One last point, I have it on good authority (Wikipedia, naturally!) that Port Des Morts is named after a battle between the local First Nations tribes, not due to any particular nautical conditions. Nevertheless there are a lot of wrecks there, especially from the age of commercial sailing ships. Which brings me to my real point - deadly to SHIPS, no one even cares about boats like ours. The aids to navigation and the NOAA charts are all designed to protect ships in those waters and say next to nothing about hazards that affect the small boat skipper. Take, for example, Portage Bay on the Lakeside of the Garden Peninsula. Looks great on the chart, protected from all points of the compass (check out the shoals to the east, yup! well protected):
https://charts.noaa.gov/OnLineViewer/14908.shtmlOnly problem is that the bottom is flat, solid ledge, no holding at all. Check out this trip report:
https://www.argobuilder.com/sailing-from-door-county-to-the-up-michigan.htmlChart 14908 doesn't show the bottom characteristics for Portage Bay at all. Why not? Because no real ship is ever going to go in there, even though it's plenty of water for our Daysailers. Make sure to get local knowledge, and read any cruising guides you can find. Get a good charting app such as Navionics (sorry about the advertising!) which has user-generated notes about various anchorages. Anyway just remember that the Lakes are Great, our boats are small and plan accordingly.
Just not to be all gloom and doom, I'll note that I've sailed in heavy steep chop (4 foot breakers) with no problem. The DS just dances over it, you'll get some spray but nothing dangerous. Make sure that the boat has enough positive flotation in her for the worst case (capsize or swamping), otherwise just be sure to sail conservatively. Your proposed crossing looks like great fun, and I'm jealous that you're anywhere near those waters.
Fair winds!