Actually, as you drive down from Milan, particularly if you're on the A1, you'll be going through the Apennines mountain range and suddenly come out into the north of Florence, without much of a chance to see the hilly countryside that characterizes Tuscany. You'll see more of that south of Florence so once you're here, make sure to plan day trip into Chianti to see the more traditional Tuscan landscapes -- head from Florence to Montespertoli, then on to Certaldo for great views, or down to Greve in Chianti on the SS222.