San Gimignano is one of the sites I knew I had been to as a kid, but never counted as visited. The simple reason was that all I remembered from the visit was the wild boar dish we had for dinner; it was delicious I believe.
I had tried some years ago to right this wrong and combine San Gimignano and Siena in a day trip. But Siena's charm had gripped me and I decided to forego the trip to San Gimignano and spent the full day in Siena instead.
Several years had passed when I finally arrived in San Gimignano. My expectations were rather high. This is the iconic fortified Tuscan mountain town. And truth be told: It's quite a site from the road when you pull up the hill by car or bus with all the towers rising to the sky from the city. Still, having been to Siena it felt rather underwhelming. It's really touristy and pretty small. In addition, there are plenty more Italian hill/mountain top fortified towns on the list and I can't really tell how San Gimignano distinguishes itself from other sites such as Pienza or Urbino, let alone Assisi.
Getting There
The closest train station is Poggiboni/San Gimignano. The city is another 12km from the station. There are busses running uphill directly in front of the station. You can buy the bus tickets at the bar in the train station. To save yourself the hassle also buy the return ticket. If you plan to return to Siena, you can continue on the same bus that is going down to Poggiboni from San Gimignano.
Buying tickets on the bus is possible, but you will pay more. The system is quite simple: The drivers only sell 2€ tickets and you need to buy as many till you reach or exceed the cost of the trip.