Episode #199: Perfect Pienza – Hilltop town of dreams in Tuscany’s Val D’Orcia

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Nestled in the heart of Tuscany, Pienza is a charming hilltop town that embodies the essence of Italian Renaissance architecture and culture. Known as the ‘ideal city’, Pienza was designed and built by Pope Pius II in the 15th century as a model Renaissance town. With its picturesque streets, stunning views of the surrounding countryside, and delicious local cuisine, Pienza is a must-visit destination for anyone traveling to Tuscany.

Show notes

In this episode, we welcome back Tuscan born and bred tour guide Debora Bresciani to talk about the walled hilltop town of Pienza. Often known as the ‘Ideal City’ and the ‘City of the Light’, this alludes to how perfect you will find this place and its views when you visit. We explore the history, attractions, and hidden gems in this town that has enchanted so many visitors with its beauty and charm, its views and quirkily named streets. For foodies, the aroma alone will draw you to the Home of Pecorino. 

What you’ll learn in this episode

  1. Pienza is found in the southeast part of Tuscany. It is in the province of Siena, in the Val d’Orcia area. This small but perfectly formed town is found between Montepulciano and Montalcino – both known for their amazing wine
  2. It is surrounded by what we think of as the typical Tuscan landscape – with the rolling hills, cypress trees and little hilltop towns
  3. Pienza is a small town within a city wall. As you walk into the city through the first gate, and down the main street, you arrive in the main square, Piazza Pio II, where you are surrounded by buildings from the Renaissance. After the piazza, you go down a small street and arrive in front of the fantastic view of Val d’Orcia which has the classic view of the Val d’Orcia – the winding cypress road (as you see in the film Gladiator)
  4. As well as being gorgeous, it also makes a great base. Within a 40 – 50 minute drive you can visit Montepulciano, Montalcino, San Quirico d’Orcia, Monticello, Bagno Vignoni (famous for their thermal springs) – places which are all very different from each other
  5. You are just 1 hour from Cortona, Siena and Arezzo and 1 1/2 hours from Florence. Pienza is a couple of hours from Rome so a day trip would not be ideal from there.  To explore you are realistically going to need to hire a car of a private driver
  6. It’s a great choice for a day trip from Florence, but it really is worth it to spend a night or 3 there. It doesn’t have big hotel chains so all options are pretty charming – there are a lot of very nice bed and breakfasts and boutique hotels or villas or farmhouse agriturismo in the surrounding countryside. They are usually pretty reasonable prices too
  7. If staying in town, many of the properties have classic wooden shutters – so you can get the amazing experience of pushing the shutters open onto stunning views
  8. Pienza has an interesting history and is known as the Ideal Renaissance city as it was built with the intention of being just that. Pienza is actually the new name of the town. It used to be called Corsignano until the beginning of the 15th century, when Enghelberto d’Ugo Piccolomini, who was born there, became Pope(Pio II). He decided to change Corsignano, re-shaping it into the city we know today – the ideal city of the Renaissance
  9. The new name, Pienza, means the city of Pius. The city was rebuilt, on the site of Cortignano between 1459 and 1462. In just 3 to 4 years during the Renaissance period. In the main piazza, you have the cathedral the cathedral in Renaissance style, rebuilt on a previous parish church. You also have a Borgia building and the Piccolomini building which looks a lot like Palazzo Strazio and Palazzo Medici Riccardi in Florence and Il Palazzo Communale, the town hall, looks like the Palazzo Vecchio also in Florence
  10. The idea of the Pope with this project was to make Pienza become the ideal city, the Renaissance example of a Tuscan city. The project finished quite early – in 1462 because the Pope died, leaving a few parts of the city from the Middle Ages and not re-built
  11. There are some interesting street names in Pienza – Via dell’Amore (street of love), Via del Bacio (kiss street) and Via de la Fortuna (the street of fortune)
  12. Pienza is built, like many Italian towns, on top of a hill and its buildings, like the bell tower of the cathedral, are made of a particular white-yellowy stone – Travertino which comes from Rapolano di Terme
  13. Pienza being in Tuscany, food and wine is an integral part of the town.  There is incredible quality wine from nearby but the food that Pienza is famous for is Pecorino di Pienza – the delicious sheep cheese which comes in a myriad of varieties, as you’ll find in the cheese shops and stalls on a visit to Pienza
  14. When you arrive in the city through the gates, the first shop that you see is a lavender shop, so you get the scent of lavender, but then as you fo further, you start to smell everywhere the pecorino cheese. It doesn’t get better than finding somewhere to sit in the city walls with a delicious glass of wine and some pecorino – quintessential Pienza!
  15. The classic serving of pecorino is covered with tomato sauce. There are lots of ways you can have it which can depend on the pecorino, like how long it is aged. Like wine, you can have seco (dry), and semisec (semi dry). You can have it aged under a grape skin, truffle or pepper. You can be sure that the quality of the pecorino is always good in Pienza
  16. Because it’s sheep’s milk and not dairy, pecorino is also good for people who have got a lactose intolerance. It is generally much easier to digest than cow’s milk cheese
  17. If you stop at any restaurant in Pienza, the typical dish is Pici cacio e pepe. Pici is a typical Tuscan pasta, like a thick spaghetti. Cacio e pepe means the pecorino cheese and black pepper
  18. In September there is a festival and Cacio al Fuso is a race they have in the main piazza where they race with a roll of Pecorino. The town is decorated with dried flowers and it is a beautiful time to visit and wander the streets
  19. Piccolomini Palace was the typical Renaissance building that the Pope built for himself and his family and he clearly chose this location to get the very best view of the surrounding countryside. It is now a museum and a ticket will let you look around, not just the rooms the family lived in, but to the private garden they have at the back – with incredible views over the Val d’Orcia. This is where you see the view of the classic photo of Tuscany – with the cypress tree road. 
  20. Debora describes Pienza as a small and sweet copy of Florence. Whilst Florence is always beautiful, unfortunately, as one of the main destinations people want to visit in Italy, it’s gone from being very busy to crazy busy. So much so that it is getting hard to even see the city. Places nearby like San Gimignano are also getting pretty crowded. But Tuscany is a very large region and it is worth going that little further to see equally as beautiful but less crowded places
  21. Pienza is not going to be as busy as somewhere like San Gimignano, because San Gimignano is quick and easy to get to from Florence, but it is by no means un-discovered and it does get busy at times – particularly around 10/11 in the morning when the buses come in. It can be good to stay at least one night to get to enjoy it when the day trippers have gone
  22. If you organize to stay 2 – 3 days, as well as exploring the Val d’Orcia area and visiting some wineries, you can enjoy Pienza in the evening when you can have a relaxed and peaceful time – and particularly enjoy the gorgeous sunsets
  23. Pienza is unique in many ways. As well as being built as the perfect town, it has double UNESCO status. The town of Pienza is UNESCO, and the Cypress Road is as well
  24. It is a great location to do a uniquely Italian tour, on a Vespa or in a Fiat 500 
  25. Although Pienza can get busy at times – you can always find a little spot of peace and quiet there to enjoy the view
  26. Debora also likes to spend time outside the gate. When you first arrive there is a public garden and if you follow the street near the public garden, you get to this old street where you can sit on a bench and enjoy a fantastic view – away from any of the bustling town life of cafes and shops etc
  27. Inside the walls, right inside the piazza she really loves going across the Via de la Fortuna and the street of Love where there are some nice cafes where you can sit, and drink something in front of the postcard views of Val d’Orcia
  28. Pienza was designed as the perfect town and we would argue that they have indeed achieved that dream

About our guests – Debora Bresciani

Debora Bresciani was born and raised in Arezzo, in the heart of Tuscany.  Driven by curiosity and interest in getting to know the cultural and historical aspects of her city better, 2017, she became a licensed National Tourist Guide in Italian, English, and German.
She shares the art, history, monuments, food and wine traditions, and folklore that the Arezzo area has to offer. And as well as sharing the treasures of her city, she also can help visitors explore further around the territory of the Province of Arezzo – with the beautiful valleys of Casentino, Valdarno, Valtiberina, and Valdichiana and the famous villages of Anghiari, Lucignano, Stia and Castiglion Fiorentino. Debora can create the perfect personalized itinerary according to your interests and needs.

You can find Debora on these channels:

Places mentioned in the show
  • Pienza – Tuscan hill top town in the Val d’Orcia
  • Castiglion Fiorentino – pretty village between Cortona and Arezzo
  • Lucignano – small Tuscan town, built in an elliptical shape. Known as the “pearl of Valdichiana”
  • Cortona – beautiful Tuscan town, made famous by Frances Mayes memoir and the film Under the Tuscan Sun
  • Province of Siena – a province in Tuscany with the capital city of Siena
  • Val d’Orcia – a region of Tuscany, central Italy, which extends from the hills south of Siena to Monte Amiata
  • Montepulciano – a medieval hilltop town in Tuscany, famous for its wines
  • Montalcino – town known for its wine in the province of Siena
  • Piazza Pio II – main piazza in Pienza
  • San Quirico d’Orcia – town named in honor of Saint Quiricus
  • Monticellopretty Tuscan town
  • Bagno Vignoni – hilltop town famous for its hot springs
  • Palazzo Borgia – which houses the Diocesan Museum of Pienza
  • Palazzo Piccolomini – a palace in the town center next to the Duomo, one of the earliest examples of Renaissance architecture and home to a museum with a garden with exceptional views
  • Palazzo Strozzi, Palazzo Medici Riccardi  – palazzi in Florence
  • Rapolano Terme – thermal town in Tuscany famous for its Travertine stone

Food & Drink

  • Pecorino di Pienza – the town’s amazing sheep cheese 
  • pici cacio e pepe – classic dish of cacio e pepe, pecorino and pepper, but with Pienza pecorino, local pepper and pici pasta – a thick, long pasta
  • Cacio al Fuso – pecorino festival in September in Pienza where they race, rolling the cheese through the piazza


  • Gladiator – famous movie where a former Roman General wants vengeance against the emperor who murdered his family and made him a slave
  • Enghelberto d’Ugo Piccolomini – received the fief of Montertari in Val d’Orcia from the emperor Frederick II as a reward for services in 1220
  • Travertine – a kind of limestone in white, tan, cream-colored

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