There has been a lot of disparaging press about Poggibonsi, and it really can’t be said to be one of Tuscany’s most exciting towns. Poggibonsi does have its own history that dates back further than the Middle Ages to Roman times, however, the majority of the town was built in the 60's and 70's with predictable architectural results.
But, all the same, there are still some attractions in Poggibonsi. Like for example, the pedestrian street in the centre, which is charming and refreshingly tourist free, even in high season. The knights’ temple complex La Magione, where medieval pilgrims stopped on their way to their holy destinations, is also definitely worth a visit. Poggibonsi also has a wide variety of restaurants, cafés and shops (not least the huge COOP supermarket), and the town is also a hub for public transport in central Tuscany.
If you are taking a trip to San Gimignano, the bus leaves from the town. You can quickly get to Siena and Florence from the town by train, although it would often be more practical to take the bus to these towns instead as it is quicker and more direct.