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Italy Train System?

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Hello all,

I am planning my trip to Italy in May and will be stopping in the major cities (Venice, Florence, Rome, and Naples) as well as visiting Siena (for a little wine tour) and lastly, the Amalfi coast (we reserved a hotel in Positano).

Originally we planned to rent a car and drive the whole way down, however, after much research we decided that would not be the best option, especially since most of our time would be spent in the major cities. Since we will be traveling by train, I am curious as to the best approach for purchasing tickets/reservations.

-Should we buy in advance?
-What is the best train system for our trip?
-Should we buy a pass or purchase each ticket individually (based on our trip outlined above)?

Your help is greatly appreciated!

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