You a fellow Kentuckian? I’m not that far from Pikeville. We live in the Piedmont, not the mountains proper. Better and more arable land. The mountains are more easily defended, but the food supplies – especially wild game – are not as plentiful as here in the Piedmont. Still, we’re only a stone’s throw away.
You trying to make it from SW Florida to the Bluegrass without using major arteries will be a challenge. Only so many ways you can go in Florida… things open up once you hit Georgia or Alabama, but then your choices limit themselves once you hit Tennessee – only so many roads through those mountains if you want to stay away from the major metro areas. Stay off of I-75. I wouldn’t even use old US 27. Everyone who ditches off of 75 knows about 27, so that will be just as bad, I think… might want to get a couple really humungous maps and try to plan a route that uses tertiary roads, logging roads, etc… stuff hardly anyone knows about. I wouldn’t go near Jellico either.
The wicked flee when none pursueth..." - Proverbs 28:1