Siena to Pienza and Montepulciano

Jessica Miles

New member
Hi there! We are renting a car in Siena and spending 1 night in Pienza and then 1 night in Montepulciano. I'm looking for driving directions for how to get from Siena to Pienza, Pienza to Montepulciano and then Montepulciano back to Siena. We prefer to take the more "scenic" routes and possibly different routes. It is very hard to find driving directions that are easy to understand, so your advice is much appreciated.

Thank you so much.


New member
Driving in Tuscany

For driving directions in Europe and the UK, we bought a portable GPS several years ago, and we've been saving spots we like as favorites ever since (we live in the mountains in central California). It's great, because when my daughter went to Tuscany two years ago, we loaned the GPS to her, and she was able to access quite a few of the locations (e.g., easy parking in Volterra, train station in Pontedera, rental car location in Florence, etc.). We bought a Tom Tom, but any of the others (e.g., Garmin) will do as well; now with Goggle maps on smart phones, you may also go that route (pun intended).

We enjoy driving in rural Tuscany. It's low-stress driving in beautiful country, with fabulously friendly folks!
Beautiful back roads from Siena to Pienza to Montepulciano

I love this way to get to Pienza from Siena:

Taverne d'Arbia
San Giovanni d'Asso

And then a beautiful back road to Montepulciano:

Pienza (south on SP18) and turn left on SP88 to go to
Monticchiello (but before you reach the village center, turn right to stay on SP88)
when you reach SP146, turn left to go back to Montepulciano.
Last edited:


The Tuscan Expert ;-)
Staff member
I also love the back road from Pienza to Montepulciano through Monticchiello.

I would suggest passing through San Quirico d'Orcia on your way to Pienza, it has fabulous postcard views of the Tuscan countryside.

I also recommend using Google Maps function to "save" spots and send to your phone, if you're using that for route mapping instead of a GPS. We also do as EdB does, saving points and then having them on the GPS but lately Google Maps app is just faster for searches when you forgot to save something! :D
But if you do search for things ahead of time, it makes sense to save them so you don't need to search later -- and Google Maps APP lets you download maps for of an area for OFFLINE use which saves on data, another important point.