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Italy - Travelling by Train - Need Help

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I will be traveling in Italy and need help with my train accomodations. Here's my iteneray:

1) Arrive at Fiumicino airport Rome at 4:10 pm local time. Need to take the train from the airport to Rome Termini station to head to Naples. I am all set with that train but need to know how much time I should allow between the time I arrive and board my train from Termini station to Naples?

2) What is our best bet for 1st class tickets travelling on the high speed trains throughout Italy? Should I book my city to city passes separately or buy a multi pass? We will go from Rome to Naples, Naples to Florence, then Florence back to Rome. Thoughts & help please?

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