Yes, totally, reading up on some of the history of the land, and then riding through it, makes the ride way more interesting. To ride Texas Hwy 90 west of the Pecos thru the eyes of Judge Roy Bean, to ride the Chiracahuas knowing a bit of history of the Apaches, that kind of thing makes the ride better
But there are always surprises. Who would have ever imagined something like Carhenge would show up near Alliance Nebraska? Not me...
Here is the route that I am (planning / hoping ) i can do...
Are you checking out Key West??
I think you'd have a lot more fun doing a trip on more interesting roads, even if it isn't as many miles.

Not quiet sure... I know it's a 7-10 miles bridge... all depends if it was super windy I wouldn't
I'm sure that this trip will be a life changing experience... if I made it through all that... I can walk on the water... lol
I'll take it easy... and won't over load myself... at the end it's all for fun...![]()

I'll second what others are saying and heavily suggest you re-think doing so many interstate freeways. You'll be missing out on so much and bored as hell most of the time. And I'm not just talking about twisty roads (although that too). From freeways, much of the US looks the same these days, with the same chain restaurants and rest stops.