While it is possible to get to Montalcino by bus, the best way to get to see the beautiful surrounding area is to drive. Whether it be driving up the winding hill roads or visiting sites or other close by towns, you have much more flexibility with a car.
You don't want a big car though. The roads are narrow and winding, so a smaller car is a lot easier to maneuver.
We rented ours through Auto Europe for about 60 Euro a day.
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. Though, 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 Montalcino involves lots of winding roads and stunning Tuscan scenery to enjoy. Cars are allowed to drive through the centre of town, though some roads are limited to residents only, and parking is fairly scarce, so you may need to park outside the walls.
We stayed two nights in Montalcino and the hotel had free parking. We had to just pull over outside the hotel (easier said than done as the road was very narrow!) and then the hotel owner would park the car for us.
If you are not driving to Montalcino, you can catch a bus from Siena. There are around 6 services a day and the trip takes about 1.5 hours. Buses arrive/depart from Piazza Cavour.