Pearl - Not much time right now but I may have some ideas for you.
One trip I enjoyed was having the boat trailered to Cincinnati on the Ohio River where I started a trip that took me eventually down the Tombigbee Waterway to Mobile, Alabama. We were to have then crossed the Gulf and eventually get to Marco Island, FL until an approaching hurricane wrecked that plan but that is a whole other story. I still have my charts and cruising guides that you would be welcome to.
Buoy shared a good idea when he said to document your trip. I used to keep diaries and paste pictures in them. Kinda nice to pull out some years later and relive. Also when you go to the Toronto boat show this winter flip thru some of the cruising guides which are invaluable on trips like you are considering.
Contact me sometime and I would be happy to share some ideas with you.