You might want to consider doing the inland waterway in the lower peninsula of Michigan for an adventure. We started near Conway, MI on Crooked Lake (close to Petoskey), to Crooked River to Burt Lake, to Indian River back to a lake (Mullett Lake), to finally hit the Cheboygan River and come out on Lake Huron at Cheboygan on the eastern side of the state. About five years ago, my wife and I did this route - took about 5 or 6 days if I remember right. We then continued on to the Straights of Mackinac (sailed under Mackinac bridge so we could say we were in Lake Michigan). We brought the boat out at Mackinaw City where the marina had transient slips (no room on Mackinac Island although we sailed into the harbor several times and around the island one day before pulling the trailering). We did this on a Hunter 216. Was a great trip and adventure. Without a galley or overnight accommodations on our 216, we used hotels and lodges along the way for overnighting and ate off boat in the towns we passed. If you consider this, you will need to check the locks along the way for clearance (one is a 'clam type' of lock). We needed to bring our mast down (there is a yoke on the 216 for laying the mast on) while keeping the bottom pinned. Worked well for us and we thought it was worth the effort. Anyone considering the Michigan Inland Waterway, should find a copy of "Navigation Charts of the Inland Route and the Straits of Mackinac" (Mapping Unlimited, 6235 Crystal Springs Road, Bellaire, MI 49615). I also had located a book that described taking the route 20+ years previous (power boat) but many of the same restaurants and information applied. Sorry can't remember the name of the book. Fun trip, cool temps, great scenery, good food and lodging. By the way, I normally sail on the Mississippi River in the Quad Cities area (Moline, IL - Davenport, IA). It would be an experience and fun too but temps in summer are in the 80's-100's.
