Southern Tuscany Exploring Pienza and Montepulciano

Southern Tuscany: Exploring Pienza and Montepulciano

On a road trip through Italy, most travellers decide to spend their time in Tuscany in cities like Florence, Pisa, and Siena. On my first trip to Tuscany, I did the same. However, when I did a road trip through Italy by campervan last June, I visited another part of Tuscany: Southern Tuscany.

I can’t believe I haven’t visited this region sooner. Southern Tuscany has anything you might wish for. It has lovely villages, stunning views, and amazingly good food. I explored two small villages on a day trip to southern Tuscany: Montepulciano and Pienza.

Table of Contents

  • Why should you visit Southern Tuscany
  • Val d’Orcia
  • Pienza
    • History of Pienza
    • Things to do in Pienza
  • Montepulciano
    • Things to do in Montepulciano
  • Other places to visit in Southern Tuscany
  • How to get to Southern Tuscany
  • Where to stay in Southern Tuscany

Why should you visit Southern Tuscany

Firstly, you might wonder: why should you visit southern Tuscany? In my opinion, this part of Tuscany feels a bit like the real Tuscan countryside that you encounter in films. Drive through the fields, admire the typical Tuscan cypress trees, and you’ll see what I mean.

Moreover, the villages that you find in this part of Tuscany have a completely different feel compared to cities like Florence and Pisa. Oh, and did I mention that the food is amazing in this region?

Val d’Orcia

The Val d’Orcia extends from the hills south of Siena to Monte Amiata, some 20 kilometers from Lake Bolsena. That means that it covers a large part of Southern Tuscany. The nature you can find in this area is stunning and has therefore been inserted into the UNESCO World Heritage List. UNESCO describes the beauty of the region this way:

The landscape’s distinctive aesthetics, flat chalk plains out of which rise almost conical hills with fortified settlements on top, inspired many artists. Their images have come to exemplify the beauty of well-managed Renaissance agricultural landscapes. (source)

I couldn’t say it better myself! Even when you don’t have time to visit a city or town in this part of Tuscany, make at least sure to drive through the Val d’Orcia. You’ll definitely want to take some photo stops along the way.


On our day trip to Southern Tuscany, we headed to Pienza first. There are two important reasons why you shouldn’t skip Pienza when you’re in Tuscany. Firstly, Pienza is a paradise for food lovers. The pecorino cheese that originated in Pienza is one of the best in Italy! Secondly, the town has a very peculiar history: Pope Pius II, who was born in Pienza, rebuilt the entire town as the perfect Renaissance town.

History of Pienza

Before the 15th century, Pienza was called Corsignano. In 1405, this town gave birth to Aeneas Silvius Piccolomini, who would later become Pope Pius II. When he became Pope, he decided to rebuild the entire town as the perfect Renaissance town. Furthermore, he renamed the town Pienza after himself (Pienza means ‘city of Pius’). To be fair, wouldn’t you like a town named after you?

Things to do in Pienza

Pienza isn’t large, so you don’t need a full day to explore everything this village has to offer. However, if you like good food and wine, you should definitely have lunch in this village!

Buy (and taste!) some Pecorino cheese

You shouldn’t just admire Pecorino with your eyes, but also with all of your other senses. Go to one of the various shops that sell Pienza’s pecorino cheese and smell the cheese. Furthermore, you cannot leave Pienza without having tasted pecorino! Besides several shops, there are many lovely little restaurants as well where you can try pecorino cheese with some famous wine of the area.

Visit Piazza Pio II

You can find the heart of Pienza at the Piazza Pio II. Various important buildings can be found here as well, such as the Palazzo Comunale. The bell tower may remind you of other Tuscan architecture.

On the west side of the square, you can find Palazzo Piccolomini. This palazzo was the summer residence of Pope Pius II. It is one of the first examples of Renaissance architecture and very elegant. Nowadays, it is a museum. Across the Palazzo Comunale, you can find the Duomo.

Entrance to Palazzo Piccolimini is 7 euros for an adult. From 15 March until 15 October, the museum is open from Tuesday until Sunday (10am-6.30pm). The rest of the year, the museum closes at 4pm.

Explore Pienza’s streets and houses

Pienza is a village where you end up wanting to visit every street, corner, and alley. Try to get lost and discover hidden corners. Since Pienza was designed by one person, it feels like a unity. Nothing feels out of place.

Lastly, you should enjoy the beautiful nature of this place! If you walk to the back of the Duomo, you’ll have some spectacular views of the Val d’Orcia.


When we’d explored Pienza, we headed to Montepulciano. You can find Montepulciano 15 kilometers east of Pienza. Again, this town is famous for food. Or actually, drink. Montepulciano is famous for its wine. Make sure to taste some! Situated on a narrow ridge of volcanic rock, Montepulciano towers over the valley.

Fun Fact: did you know that Montepulciano was used as a filming location for the Twilight movie New Moon?

Things to do in Montepulciano

Like in Pienza, tourists have discovered Montepulciano. Nevertheless, this town is way less crowded than cities like Florence, Rome or Venice. Tourists won’t hinder your experience of this part of Tuscany.

Enter the old town from the Via di Gracciano nel Corso. If you start your exploration of the city at this point, you can basically walk one long street that will eventually take you to the Piazza Grande. On your way, you’ll encounter various churches and palazzos.

Try the local wine

Tasting wine in Tuscany should be on your Italy bucket list, and since this area is famous for its wine, you can’t go without tasting some in this lovely town! There are various places in Montepulciano where you can taste wine. You can also opt to have dinner (with some good wine of course) in Montepulciano.

Piazza Grande

Piazza Grande is the central square of Montepulciano. The views from the tower of the Palazzo Comunale are absolutely stunning. The tower literally towers above the town. This building might also remind you of architecture in Florence.

Did you know that Montepulciano has been a loyal ally of Florence during the Renaissance? This may explain why the architecture of the Palazzo Comunale looks so familiar!

When we arrived at the square, there was a procession of kids in traditional clothing taking place. We didn’t find out why the procession was taking place, but it seemed like the complete village had turned out. It was funny to watch though.

Other places to visit in Southern Tuscany

  • Chiusi: on the border between Tuscany and Umbria, you can find Chiusi. Like Pienza and Montepulciano, this is a very old town. However, the real attraction of this village is its archaeological museum. The museum is not large, but has a good collection of Etruscan artefacts.
  • Montalcino: a medieval town in Southern Tuscany which is, like Montepulciano, famous for its wine: the Brunello di Montalcino.
  • Siena: when you’re in this part of Tuscany, you can’t miss a trip to Siena! Its Piazza del Campo might be the most impressive square in all of Tuscany. Moreover, I found the cathedral of Siena the most beautiful cathedral in Tuscany (even more beautiful than the Duomo in Florence!).

How to get to Southern Tuscany

Siena is probably the most famous city of Southern Tuscany. You can find Pienza and Montepulciano 60 kilometers from Siena. A day trip to Pienza and Montepulciano is certainly possible from Florence as well (110 kilometers). Rome is 180 kilometers away. The nearest airports are in Perugia and Florence.

Where to stay in Southern Tuscany

If you’re looking for a base to explore a large part of Tuscany, I would recommend staying in Siena or Florence. However, if you’re doing a road trip through Italy, I would recommend staying in one of the many lovely villages in southern Tuscany. Pienza and Montepulciano offer various places to stay. You can also opt to stay in Chiusi or Montalcino.

There are also day tours to Pienza and Montepulciano departing from Siena.