Sounds like a grand adventure, JeZ, and well worth the effort. Amtrak is a great way to go; maybe you can use the train as your main routing tool and use the occasional rent a car to get to some of the places that the train doesn't serve.

If I were doing it, it would look something like this: Boston, New York, Toronto, Philadelphia, Chicago, Minneapolis.

From there I would definitely take the train across the country to Seattle - it is a spectacular ride. From Seattle I'd go down the coast - San Francisco, Los Angeles. At this point you start back east: through New Mexico & Arizona to Austin, Texas.

Austin to New Orleans, up the Mississippi to Memphis, due east to Nashville. From Nashville you can wander Southeast through Atlanta, Valdosta (Georgia) and into Florida.

If you wanted to go east from New Orleans to Florida, through Charleston, that would be worth it, too.

There is soooooo much to see; this is the whirlwind tour and you will get no more than a taste of each place. Another way to do it is to pick a handful of places and spend some time in each. Any way you choose to do it, you win!

Have a great trip! Bon Voyage