Heya, Doug!
Naw, take to damned long to actually sail there. I'd have to cross the length of Lake Michigan, cut through the NW of Lake Huron, then (likely motor due to traffic) through the passage into Lake Superior. Then, of course, I'd then have to transit the legth of Lake Superior! Certainly sounds awesome, and I shall do that one day, but... alas... as a working man, I simply cannot take a couple of MONTHS off of work.
As such, I'll be towing my Santana 2023 up there. Sure can't beat leaving early in the morning, launching, and being on the water late that same afternoon! When I was looking to buy my vessal, I intentionally looked for and purchased something that I could TOW. Didn't like the idea of being locked in the Milwaukee area like the rest of these scrubs that hang out around here

(just teasing at you guys, you know that!)
I like the idea that I can be launching in the Carribbean the same day that I depart. Lake Nippissing, Georgian Bay, Lake Huron, North Channel, Apostle Islands... hell, everything is within striking range. Likely the biggest purchasing point of my vessal was that I could tow it. Had never seen a Santana 2023 before, checked it out due to curiosity. Goodness, my tow weight of the boat (dry) is only 1,580 pounds!
Anyway, when you do Door County (great time), I'd suggest launching at Fish Creek. They have free parking for your rig and vehicle behind the Post Office for however many days you want.
Let me know if you're interested in the Apostle Islands for next summer, perhaps we can carravan up there. Either way, looks awesome sailing, great scenery to be seen.
Since you have the flexibility of actually going somewhere (towing), I'd suggest you contemplate the North Channel, too. Simply fantastic, and a great launch site is @ Spanish, Ontario. If you ever decide to head that way, let me know, and I'll point out a few spots for you on my charts!
Anyway, anyone here ever done the Apostle Islands? Points of interest? Input?