Toscana by train

There are many towns that can be visited by rail, but San Gimignano and Pienza are not part of that list. For San Gimignano you can take the train to Poggibonsi, then there is a bus shuttle to San Gimignano, Pienza is further from the closest station (Chiusi). If you plan to stay multiple nights in those towns you should consider a car. If you like to visit by train stay in Florence. Siena is also a good base to visit the many towns in its province, but more than the train, you will be using buses from Siena.

Neither San Gimignano nor Pienza has a train station, so side trips purely be train from those places will not be possible. I think the nearest train station to San Giminano is in Poggibonsi. It appears there is no train station within 15 miles of Pienza. So every trip you take from either of your bases will start with a bus ride to a larger town with a train station. Edited to add: I should have said "nearly every trip" and "...unless there's another place you want to see on the same bus line".

It is not easy to see the small towns of Tuscany without a car. It is especially not easy to see more than two small towns in Tuscany on a single day without a car--unless you sign up for a tour. The transportation that exists tends to fan out from the nearest city of size, not necessarily linking multiple beautiful villages of interest to tourists. I believe most tours to rural Tuscany depart from Florence or Siena.

Here is website with a good, if simple, map of Tuscan towns served by rail and connecting buses.

https://www.wanderingitaly.com/maps/tuscany-rail-map.html

It doesn't show all options especially by bus that is not train connected - I know Greve has a bus from Florence and you can connect Arezzo and Siena by bus much faster than by train - but it's a good starting point.

=Tod

Hired an,
That's a great map, thx so much.