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Train tickets

We will be on the move while in Italy. We will travel from Verona to the Dolomites, where we will get a car, then train to Venice, then to Florence, Sorrento and to Rome. As many stops as we are making would it be cheaper to buy a rail pass for Italy or to purchase each trip separately at the station? There will be eight of us traveling together.

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Trenitalia offers a discount on point-to-point tickets for families. Are there any children in your party of eight? If so, what are their ages?