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Traveling from Nice to Tuscany

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A friend of mine is planning on renting a villa in the fall in either Umbria or Tuscany. I was thinking about going to Nice, France first for three or four days and then taking a train to Italy. What would make the most practical sense? I live in Chicago. Fly to Nice, take a train to Italy then perhaps fly back out of Rome? Also, how long is the train from Nice to Florence/Umbria. Would it make more sense to take the train back to Nice and fly back on the return round-trip ticket? Thanks for any input.