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Day road trips around Sienna

I am looking for a couple town recommendations for some road day trips from Sienna.

Our family of five will be spending 3 nights in Sienna in the middle of our two week vacation. We are picking up a car at the Florence airport big enough for three adults and two kids with carry on luggage only and driving to Sienna. We've got a hotel in Sienna outside the pedestrian zone with parking.

We'd like to take a day exploring the area to the south/southeast of Sienna one day, and then a second day exploring the area to the northwest (perhaps San Gimignano, Volterra). Looking for some recommendations on two or three towns/villages to visit in these two areas.

We will be picking up our car in the morning from the Florence airport and plan on driving south through the Chianti region as we make our way to Sienna for the first night.

The goal of the three nights in Sienna is to explore the Tuscany region a bit while using Sienna as a base. Think we can accomplish that with this plan?

Thanks!

Posted by
7272 posts

To the south and southeast of SIENA
Montepulciano, Pienza, San Quirico, Bagno Vignoni, Montalcino- the Val D'Orcia region etc
All worth a stop

Posted by
3313 posts

Can’t help with the Chianti portion but hopefully Suki will see your post and comment. I rented a car in Siena and got on the Sienese Crest Road which is considered one of the most beautiful in Tuscany. The landscape consists of rolling hills with many landscapes.
Good stops along the way are Pienza’s old town (1h 15m) and afterwards continue to Montepulciano (30-minutes). It will take another 1h 15m drive to get back to Siena.
The next day drive to San Gimignano (1h 15m) and afterwards to Volterra (45-minutes) and on this drive you’ll see more forest which is a very nice contrast to the hill towns. Siena is 1h 15m away.

Posted by
11647 posts

Drive SS 222, the historic Chiantigiana connecting Siena to Florence. There are so many charming villages to explore such as Castellina, Radda,Panzano, Greve. This starts near Siena heading north with pockets of villages off to the side.
Volterra is certainly worth a visit. Drive up and enter a garage built into the hill just before you get to the top of town. San Gimignano is interesting with it’s medieval towers. The problem is crowds and bus tours. Worth a try.
Make sure you spend enough time in Siena too( note spelling.)