I have driven Wisconsin to the Florida Keys (1650mi) more times than I can remember. I have driven straight thru a number of times but now drive about 1000 miles the first day. I will leave at 6am and drive until midnight trying to average 60 mph including stops. I would pick cities to get thru late at night when traffic is light so you won't have to deal with it the next day. Leaving Wisconsin I try to get thru Atlanta and when leaving Florida I try to get thru Nashville. Audio books are a big plus to make the trip shorter, you can buy/rent them at any Cracker Barrel restaurant and return them at another location.