It wouldn’t necessarily be a road trip although Route 66 would be my choice if I had to travel by car. But my preference would be to take a water road trip–America’s Great Loop Cruise through the waterways of eastern United States and some areas of Canada.
I’d begin in Chicago, go south along the Mississippi, then cut to the Tennessee River in my home state, then on to the Tennesse-Tombigbee Waterway to the Gulf. The Atlantic Coast would be my next adventure, traveling on the Intracostal, ducking into different ports along the way, enjoying life at the marinas where everyone is welcome. Not sure if my memory is exactly correct, but I seem to remember that two of Morgan Freeman’s greatest pleasures were working crossword puzzles and being docked at a marina. I would concur wholeheartedly.
Next stops would be New York, the Hudson, the Erie Canal. On westward to Canadian waters and to the Great Lakes and back to Chicago.
Why? Why not? Life from a boat looks so different than life from a car.