It is slim pickings up there with regards to charters. I chartered an Pearson 303 from Sailboats Inc out of Sturgeon Bay a number of years ago, but I believe they have closed that charter base. Manitowoc would be the closest. Since I believe the loveliest part of Door County is Fish Creek and north, it would be a real hike from Manitowoc to get there.
If you do find something, please post back here and let us know.
"To reach the port of heaven, we must sail sometimes with the wind and sometimes against it - but we must sail, and not drift, nor lie at anchor.”
- Oliver Wendel Holmes