Also from the WI side of the pond but we do sail the MI side regularly and frequent the area you are headed through.
First off, I will also recommend using Active Captain
for near real time info on what is available along your route. We don't have a dog aboard so frequent beach stops haven't been a concern for us. I also recommend you download OpenCPN
and Lake Michigan charts to do your travel planning.
We normally frequent marinas vs. living on the hook but that will likely change now that both of us are retired. Typical routing for us has been:
Frankfurt to Leland (35 NM) but you could drop the hook off either Glen Arbor or South Manitou Island but both locations have nothing available ashore.
Leland to Northport (26 NM) just because we like the marina and the town.
Northport to Charlevoix (20 NM) There is a fairly narrow channel between Lake Michigan and Charlevoix that has a bridge on the Charlevoix end. The bridge opens during the tourist season for only 6 minutes on the hour and half hour. The bridge is low enough when closed that sailboats can't get under but most large powerboats can. You want to time your arrival so that you don't spend too much time loitering in the channel waiting for the opening. Picture yourself trying to hold position in a wind tunnel while there is two-way powerboat traffic whizzing by. We were not impressed with Charlevoix and the power boaters think they own the waters.
Direct to Charlevoix from Leland is 30 NM.
That's about all I can offer at the moment. Our planned run to Beaver Island from Charlevoix during our last trip NE was pre-empted by a bad weather forecast and the need to get my wife back to Milwaukee for that J.O.B. thing she still had going on.
As a side note . . . MI Municipal marinas are a pretty good deal. Advance reservations are now made through a State run website. However, a simple phone call will normally get you in a transient slip on the day you plan to arrive. Cell phone service is pretty good on the MI side out to roughly 7 miles.