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 clichΓ© 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.

Read: 50 beautiful small towns in Italy

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.

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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36 thoughts on “Pienza – a hilltop town in southern Tuscany

  1. Lolo says:

    IM IN LOVE! It’s so cute!! And asking the locals is always a good idea!! It definitely pays off! Will have to pin later, I think Pinterest is having issues πŸ™ #FarawayFiles

    • Katy says:

      Lucky you Shelley. I’ll be in a similar situation in a few months so just trying to make the most of it now. We hope to live there one day too! Where did you live?

  2. Corey with fifi + hop says:

    Aaaah Pienza! One of my faves! Interestingly enough we visited on the recommendation of a local too. And it met all expectations. Your photos are stunning – the autumn light is so beautiful. #farawayfiles

    • Katy says:

      Do you like the younger or more aged cheese? I like both but always lean towards the bitey-ier versions, We brought some back for this weekend

  3. Carolyn Eddie says:

    We had a wonderful family holiday in Tuscany with some friends a few years ago. We were close to the ‘Under the Tuscan Sun’ village but also visited Sienna (which I think about about whenever I see the Copenhagen town hall) and sneaked in some wine tasting. Gorgeous part of the world.

  4. Angie Vincent says:

    Such a glorious part of Italy. I would say it is my favourite too. I had one of my most memorable lunches at Montepulciano. I love your beautiful photos. That tuscan light is stunning. #FarawayFiles

  5. Bryna | Dotted Line Travels says:

    So pretty! I can see why it would be your guide’s favourite place. It’s a picturesque Tuscan town. I love the romantic street names. Maybe if I make my way back to Italy (and have the guts to drive!) I’ll visit it for myself!

  6. Ruth | Tanama Tales says:

    Like you, I take locals advice seriously. I am glad you were pointed towards Pienza because the town is so charming. It is cute but rustic (in a good way) at the same time. The surrounding hills are just WOW. I am all about discovering small towns like this and going to lunch at the locals favorite joint. #FarawayFiles

  7. Sharon says:

    Oh my, I would love to visit Tuscany! Your photos are so lovely. I especially love the one of the cobblestone steet. What a treat to be there. On my bucket list for sure!

  8. Shelley says:

    Ohhhh, but isn’t this part of the world just incredibly spoiled by beauty, gorgeous light, and good food! It’s rather unfair wouldn’t you say? We spent some time in Montepulciano and Cortona (where Under that Tuscan Sun was filmed), last summer. Despite both places being rather touristy, we still loved it! Adding Pienza to my never-ending list of places to visit in Italy! πŸ™‚ #farawayfiles

    • Katy says:

      I think it is outrageously unfair Shelley! We missed Montepulciano and Cortona so I guess it is a return trip on the cards for me..damn… πŸ™‚

  9. Nell (Pigeon Pair and Me) says:

    Oh my. What a delectable place! I’m not surprised they chose it as a location for Romeo and Juliet. Sounds like a great place for platonic get-togethers, too. It must have been lovely seeing it with your friend. #FarawayFiles

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