Pienza – a hilltop town in southern Tuscany

Pienza Tuscany Italy

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People always say, “ask the locals” when you go travelling. It’s a bit of a cliché but I always find it pays off.

Earlier this year when I visited Brescia in Lombardy, I asked our wonderful tour guide where her favourite place was in Italy. Without hesitation she replied – “Pienza Tuscany”.

So when the opportunity arose to discover the towns of southern Tuscany, of course I put Pienza at the top of my list of places to visit.

Pienza Tuscany

Romantic streets Pienza Italy

Winding country roads flanked by vineyards, olive groves and wheat fields take you to Pienza. It’s the typical Tuscan landscape with rows of pointed Italian cypress trees lining the way to ancient villages and cantinas.

Bathed in early autumn sunlight, the countryside radiates with an ethereal glow that extends to the village itself.

Highlights of Pienza

Pienza sits on a hilltop overlooking the Val D’Orcia and from this vantage point you can see other famous hilltop towns Montepulciano and Montichiello in the distance. Monte Amiata looms in the distance.

The village has this strategic position completely by design thanks to some important former residents.

A tale of Piccolomini popes

It’s hard to believe that this tiny town of just over 2000 inhabitants played an important role in history but there are clues on every corner.

After entering the village on Corso il Rossellino, you notice an elegant palazzo just before Piazza Pio II, home to the town’s cathedral.

Palazzo Piccolomini was the home of Pope Pius II who had his home town, originally called Corsignano, remodelled and renamed after himself in the 15th century.

The design is the work of Bernardo Rossellino, the architect responsible for the magnificent facade of Santa Maria Novella in Florence.

Palazzo Piccolomini Pienza

Now a UNESCO world heritage site, Pienza was built on Renaissance humanist principles which are also reflected in the Pope’s palazzo and several other buildings of significance in this tiny town.

Take a tour of the palace to learn more about the Piccolomini popes (there were two!), view the family’s collection of treasures and take in some of the most incredible views of Tuscany from the third floor loggia.

It’s best to check their website for latest hours and ticket prices.

READ: our Tuscany guide 

Incredible views and vignettes

Pienza Italy view from Palazzo Piccolomini

Palazzo Piccolomini is not the only place for fine views in Pienza. The town’s position high on a hill means there are viewing spots around the perimeter perfect for passagiata or an afternoon stroll.

Once you have soaked up the Tuscan landscapes, take a walk and enjoy the atmosphere of this pretty town.

Ivy draped walls and perfectly potted plants frame doorways, cats slink around looking for a place to lounge in the sun and people chat over coffee or over lunch at cafes and restaurants.

Pienza well at harvest festival

We visited during a harvest festival and there were gorgeous decorations hanging from walls, and the town’s well.

Lovelorn streets

It seems many people fall in love with Pienza. And it’s hard not to.

But just in case you were wavering, even the streets have amorous names like Via dell’Amore – street of love – and Via del Bacio – kiss street.

Streets of Pienza Tuscany

The town was even the location for Zeffirelli’s acclaimed 1968 film version of Romeo and Juliet.

Pecorino – a Tuscan cheese

Pienza is famous for its local pecorino sheep’s milk cheese and you can taste and buy it at many little stores in the town. The firm cheese is aged from 6 to 18 months used in many local dishes depending on its age and the intensity.

Pecorino Toscana Pienza

The young pecorino toscano has a delicate flavour and is used in salads but when the cheese is aged and the flavour becomes more intense it pairs perfectly with fruit and the amazing local wine.

Wafts of pungent cheesy goodness follow you around every corner in Pienza and it is no wonder Italians come from far and wide to visit the town to try the cheese.

If you visit in early September you might chance upon the annual pecorino festival and its famous cheese rolling competition – Gioco del Cacio al Fuso.

How to get to Pienza

To best discover this region I suggest that you take a tour from Siena or Florence or rent a car as the public transport links in this area only serve a small community.

Tuscan cypress Pienza

The drive from Florence to Pienza is 120 kilometres and takes under 2 hours if you follow the E35 Autostrada towards Rome. Take the Valdichana exit and follow the road through Montepulciano for one of the most scenic drives in Tuscany.

Alternatively, the journey from Siena to Pienza is around an hour on the road following the Raccordo Siena-Battolle.

There are several car parks in Pienza. Most are found just outside the town’s walls and then it is a very short walk to the main street and piazza.

Exploring southern Tuscany

Val d orcia southern Tuscany

If winding roads, lines of cypress trees and those typical Tuscan hues are what you crave then why not spend a day or two in southern Tuscany exploring the villages and cantinas.

These scenes were immortalised in the book and movie Under the Tuscan Sun and I can assure you that they are every bit as picturesque as you imagine.

From Pienza you can easily reach Montepulciano, or do as we did and enjoy lunch looking over the Val D’Orcia at wonderful Osteria La Porta in Montichiello.

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