The Plan: The Great Loop. Here's a map:
This is how it works: You travel in a counter clockwise direction. The summers are spent in the North, exploring Georgian Bay's 30,000 islands, taking in the endless vistas of the North Channel and making your way from north to south on Lake Michigan.
In the autumn, you start by travelling right spanking through downtown Chicago (which will be a BLAST!!!), then down the river system, including the Illinois, Mississippi, and the Tennessee-Tombigbee Waterway, all the way to the Gulf of Mexico. There are lots of interesting side trip to take along this route if time and inclination permits. We're thinking of Nashville maybe. Or maybe we'll park the boat, rent a car and take a road trip west to the Grand Canyon for a couple of weeks. We don't know. It depends on the weather, our mood, etc. Jeff wants to take in some sporting events (hockey and baseball). I want to check out some live music (Blues in Chicago!!) and artsie-fartsie stuff. The whole point is to be flexible, go where the wind takes us, and take in as much as we can.
Once the hurricane season is safely past we'll spend the winter in the South, hanging around Florida and, with the right weather conditions, maybe the Bahamas. We think we might just find a nice marina and hunker down and spend a month or two working on our golf game, hanging out, taking in the sights. etc. etc. Whatever we do, it will be where it's warm with no snow to shovel.
Once spring hits we'll point our bow North and travel up the intracoastal waterway, which is a protected passage of rivers, lakes and canals along the East coast of the the States. We'll pass through old charming cities like Charleston and Savannah, Chesapeake Bay and we can take a side trip right to Washington DC and explore the U.S. capital while staying at "home" on our boat. We'll cruise right through New York harbour, right past the statue of Liberty, (and visit my niece, Rachel). Then up the Hudson River. From there a canal leads back to Canada where we'll maybe (hopefully) check out the Rideau canal (and Canada's capital city). That takes us back to the Gananoque area, where we'll "cross our wake", ending the circle.
That's the plan, in pencil.