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
A 4-day Italy pass for $150 plus 3 mandatory seat reservation fees for about $35 per person in 2nd class is cheaper than full-fare tickets for your route (closer to $250). But if you're ready to book the longer rides now for a discount, then the price difference shrinks. See https://www.ricksteves.com/travel-tips/transportation/trains/italy-rail-passes. Siena and San Gimignano are both better served by bus from Florence.
Siena is served by train, but the bus will get you closer to the city center.
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.