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14 day Italy trip: point to point train tickets vs pass?

My wife and I will be going to Italy for the first time in May and I'm just trying to figure out the most economical travel method. We want to take the train to most destinations, and I'm not quite sure of the difference between a rail pass and point-to-point tickets. We will be traveling from Venice to Monterosso, Monterosso to Florence, Florence to Salerno, Salerno to Rome. While in Florence we may take a day trip to Siena or maybe San Gimignano, and hopefully they are serviced by the train. In your opinion, with all of that train travel which option for ticketing would be best?
Thank you,
Jeff

Posted by
11613 posts

Siena is served by train, but the bus will get you closer to the city center.

Posted by
11613 posts

I just priced your tickets on Trenitalia for a random date in mid-May. If you buy today, the total lowest available fares come to €115, without daytrips to Sirna and San Gimignano.