Re: My wife and I have just begun talking about this....
I ask because we've been thinking about picking up some of the stretches we've missed.
We've done the ICW from Norfolk to Key West (including the Bahamas). And have made the trip to Ft Myers both via Flordia Bay and Lake Okeechobee. We've run the Gulf ICW up to Anclote Key and cruised from Carabelle to Dauphin Island. We've done some of the Mississippi near New Orleans but can't say we're fond of the levees and lack of small boat services.
We've done some Tennesee River (Knoxville to Nickajack), all of Lake Barkley/Kentucky Lake. Some waters around Nashville.
Lake Michigan from Calumet Harbor to Chicago both inside and out, then up to Detroit Harbor on Washington Island taking in every harbor on the way.
We crewed on a sailboat from Sodus Bay to New York via the Barge Canal system, then on to Beaufort NC.
Most of the cruises were on our current boat, an 18 foot cuddy,
others were on our 27' sailboat
or our 35' trawler.
The section we're looking at next is a small loop from Albany to Montreal then down the St L to L Ontario, in at Oswego and back to Albany.
Keep us posted on your plans, maybe we can share a fender somewhere.