We drove down in October from Latrobe (about an hour east of Pittsburgh). We stopped in Hilton Head on the way down, staying at the
DVC resort which is just lovely. We stopped in Charleston on the way back up. We did it that way as that was the only nights I could book in Hilton Head, but if I had a choice, I'd swap that. HH is the perfect place to relax and decompress after a Disney vacation.
It was the first time we'd ever driven down and didn't find the drive bad at all. If we do it again, we will probably add Savannah to the mix - even if it's just a day trip from HH.