Ive done both routes (not from Florida, but from Wisconsin.....usually go through Sask, but detoured once to see Mt Rushmore and the missile museum by Mitchell SD and took the Montana route from there). Can say without question the Montana route is better for scenery, the sask route is better for time, so guess its whats important to you.
As others have said, get the AT's and set of chains. If it gets wet and turns to snot on you then you'll be happy you did. or, work something out with your outfitter or host to meet you in Manning and bring you in/out and save yourself the headache or cost of new tires. Could get lucky and its dry for the duration, or could get in with no problem with your continentals if its dry when you arrive and then it rains or snows for a week and you've got yourself a journey coming out lol
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