Train pass

No need for a pass
Those will mostly be regional trains, inexpensive and never sell out
Just use the Trenitalia app

All the places you list here are reachable by train from Montecantini Terme and all are local regionale tickets. There is no need to buy these tickets until you are ready to use them - using the phone app is by far the easiest solution. The phone app also let's you check schedules and the progress of trains you're waiting for or are connecting to. Many of these are direct and run on the same line from Florence to the coast. You will probably have to change for Pisa, but that's an easy thing.

Pietrasanta is another interesting little art town near the coast of you're running out of day trips. Also Prato (interesting museums) Pistoia are on the the direct train line from Florence that loops through Montecantini Terme and onto Viareggio. Going to Florence and onto Siena would be a long day but could be worth it as well.

The tickets from Rome to Florence are fast trains and can be booked ahead of time at a significant discount by trading flexibility for price and locking in a specific train. If you're going straight from the airport to Florence then I wouldn't try and guess which train you'll need ahead of time - just book the next one and pay full price. If you're staying a night or more in Rome I would buy your Florence tickets ahead of time and save money.

There is no pass for regionale trains but they are cheap, always the same price and never sell out.

Have a great trip,
=Tod

I haven't checked the routes you'll be using but as the others mentioned, you'll probably mostly be travelling on Regionale trains. Rail passes are not usually a good value for those as tickets are quite inexpensive. Once you've decided which trips you'll be taking, you can easily buy tickets via:

• The Trenitalia website (I believe you'll have to register on the site for purchases) - tickets will be prevalidated - https://www.trenitalia.com/it.html .
• From a ticket reseller website such as TrainLine (they may charge a small service fee).
• From a staffed ticket office at the local station
• From an automated Kiosk at the local stations (these will be paper tickets which must be validated prior to boarding the train on the day of travel - failure to validate may result in hefty fines which will be collected on the spot!). I often use the Kiosks as they have an English language menu and are very easy to use.

You may have already seen this website, which has some good information - https://visitmontecatiniterme.com/ .

You may find this website helpful - https://www.ricksteves.com/travel-tips/transportation/trains/italy-rail-passes .

I often buy paper tickets the day prior to my trip if I happen to be in the vicinity of the station. It's important to make sure the right travel date is listed on the ticket. On the day of travel it's so easy to validate the ticket and then hop on the train.

If any of your rail trips will be via the "premium" trains such as the high speed Freccia or Intercity trains, these have compulsory seat reservations which are specific to train, date and departure time. If you board the wrong premium train, even by mistake, that may result in hefty fines collected on the spot. The tickets will specify the coach (carozza) and seats (posti) that you'll be sitting in.

If you're using the high speed trains, note that you can also use the competing Italo Treno line. The coaches are a distinctive maroon colour, so they're easy to spot. These also have compulsory reservations.

You might find it helpful to have a look at the Trenitalia website and check out the routes you'll be travelling on. The bahn.de website also has good information, but you can't buy tickets for travel in Italy on that site (AFAIK). That will give you an idea on which types of trains you'll be using and the departure times.

Will you be travelling with phones that have internet capability?