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Italy - Car vs Train in Tuscany

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I am traveling to Italy this year for a little over two week adventure in five cities. Our plan currently is:

Venice - 3 nights
to Milan - 2 nights
to Florence (hotel in Florence, but want to take day trip to Pisa) - 4 nights
to Siena (region) - 2 nights
to Rome - 4 nights

We are trying to figure out if it would be best to get a rail pass for traveling between Venice, Milan, and Florence, and then renting a car for the duration of our time in Florence and Siena and dropping the car off once in Rome. We just are not sure about renting a car and driving (we are okay driving in NYC, but not sure how well that correlates in terms of to driving in Italy) or if we should strictly travel via trains. Any advice would help!

And of course, we want all the recommendations we can get on places to eat.

Thank you!

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