Italy has a reputation for crazy drivers, particularly in places like Rome and Naples. As we were not visiting any big cities we decided to brave driving in Italy, and I am pleased to say it all went without a hitch.
I must admit that driving in the teaming rain on the truck-infested autostrada wasn't my idea of fun, however being able to really get off the beaten track in Tuscany was so worth it!
The drive to Montepulciano is lovely, with the stunning Tuscan landscape to enjoy. Cars are not allowed to drive through the centre of town, so you need to park outside the walls. The main car parks are near Porta al Prato. Close to the gate there is a small amount of metered parking, and a few minutes walk down the hill you will find some free parking, which is where we parked.
From Porta al Prato there are small minibuses that drives up the hill to Piazza Grande, if you are physically unable to make the climb yourself.
If you are not driving to Montepulciano, you can catch a bus from Siena (via Pienza) or Florence. Buses arrive/depart from Car Park 5, just near Porta al Prato.
Montepulciano lies some 60 km south of Siena. It can easily be reached by car. However, it's quite difficult to drive into the city. There are free parking areas at the bottom of the hill or halfway up the hill. Stairs will bring you into the fortified town.
We rented a Fiat in Rome and drove through Italy. Getting to Montepulciano was pretty easy with the help of a map.