We drive that exact route every year as we are snowbirds and leave the middle of February and return the end of March. The last two years we have had to leave a day early due to weather and tend to be ready to go at least two days ahead of time. You really have to pick your days driving during the winter due to the variety of weather patterns which occur at that time! We always cross at T.I. and drive 8-10 hours to make sure we are close to or past Washington. We have found that this allows us to beat the snow but freezing rain can be an issue in the early am! On the way down we usually stop in Winchester VA or Fredericksburg VA the first night, and Florence SC the second night. Our third day is almost 9 hours but as we can't get into our villa until 4 pm, it saves us the cost of another hotel. In the past, we have stayed a third night in Daytona Beach or St Augustine which gives you a quick 2.5 hour drive to Kissimmee! We don't pre-book hotels anymore, but use the coupon books at the State rest stops. We really try to drive during the day light hours of 7 am to 5 pm. We can't believe that we use to drive it straight through when we had to travel during March Break! I would much rather drive these days than fly, as we really enjoy setting our own pace.