We take our fifth wheel from the west suburbs of Chicago to Gulf Shores every year -- sometimes before Christmas, sometimes in January.
Our route is through southern Illinois to Paducah. First night is at a KOA there, and most years I can dewinterize then. Once we get past Nashville, it's a straight shot south on I-65. The second night is usually in northern Alabama, where I can always do it if Paducah wasn't warm enough. And the third night we're on the Gulf, just a few miles from the Florida line, in Gulf State Park.
Coming back is the reverse. I winterize in Paducah, and get home the next day.
Hope this helps.