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Venice to ??

Hi-we are travelling through Italy for the first time this September-very exciting for a middle-aged Kiwi couple!We plan on starting off in Italy in Venice, and also want to stay 3/4 nights somewhere in Tuscany and the same in Cinque Terre.If we travel from Venice by train , which of these areas would make more sense to head to?While in Tuscany we would like to base ourselves in a small town-maybe somewhere like San Gimignano- and hire a car to have a look around.We are aware that a car in CT is not a good idea.We will finish up in Rome before flying home.All ideas gratefully accepted.

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Train from Venice to CT. Then train from CT to Florence (don't skip Florence). Then, after Florence, pick up a rental car, say in Siena or Chiusi, to efficiently explore Tuscany. Turn in the car in Orvieto. Then train to Rome.