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Hit Florence on the way to Milan. There is so much famous artwork there. Id also advise at least a day in Rome to see the things there. Rome itself isnt the nicest place Ive ever been, but its absolutely worth it, especially to see the Vatican. St Peter's Cathedral is just beyond words. You wont regret it. However, the driving in Rome is just as bad, if not worse, than the stereotypes. You may do better to park the car at some town and take a train into Rome. In fact, I know you would be. No parking anywhere, the drivers there have an utter death wish, and the roads are so maze-like, even the best map in the world would be of little use. Once in Rome, the subway sucks ass--id just take a taxi. The train system works pretty well though, so it wouldnt be hard or expensive to do what I suggested and just go visit some town somewhat close to Rome and take the train in and out.
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"Good people do not need laws to tell them to act responsibly, while bad people will find a way around the laws."
--Plato
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