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To Florence from Milan or Rome

I need to get to Florence (San Casciano Val di, to be exact) but cannot get a flight into FLR or Pisa using miles. I would need to fly into Rome or Milan. I plan to get a rental car and drive to Florence. My question is this: Which is an easier or more pleasant drive--Milan to Florence or Rome to Florence?

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Thanks for the info. I have to get a rental car because I cannot get an early enough train into Milan for my flight back home, therefore necessitating my own transportation. I am also staying at a villa outside of Florence, so I need the rental car while I'm there.