Episode #139: Secret Towns Under the Tuscan Sun

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Cortona is the Tuscan town that stole Frances Mayes’ heart in her celebrated memoir, Under the Tuscan Sun. The book and the movie of the same name have inspired many thousands of people to travel or even move to Italy. 

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Show notes
We talk to Tuscan-born and bred tour guide Debora Bresciani, who knows Cortona like the back of her hand. She tells us all about the magic of Cortona but also shares some other local places in the rest of the Val di Chiana where you might find your very own sense of belonging in this very special part of Tuscany. We talk flower floats, Trees of Love, sweet garlic, and giant white cows. 

What you’ll learn in this episode

  1. Cortona is a Tuscan hilltop town that was made famous by Frances Mayes memoir and the movie that was made from it Under the Tuscan Sun, making it a popular location for day-trippers. There is a mix of medieval and Renaissance styles within the city walls and being at the top of the hill, the views from the main square are spectacular, out over the Val di Chiana. Depending on which season, you might see olive trees, sunflowers or grapes – an ever-changing, but always impressive landscape
  2. The main street in Cortona is Rugapiana (though its official name is Via Nazionale). Rugapiana comes from meaning break or split – because from this one street many alleyways lead off. As you wander along you get glimpses through to various views out of the city. You can happily spend half a day there walking around this area and can enjoy a great meal sitting in one of the piazzas
  3. Cortona is an Etruscan city, so going back to the 8th century BC – around 3000 years ago
  4. There is the MAEC (the Etruscan Academy Museum) which covers the history of Cortona from Etruscan times up until the 20th century. Roman times are often focused on more in Italy, but the Etruscan civilization came first and Romans borrowed and improved on much from them. The people in this region are very proud of their Etruscan heritage – this is when they originated
  5. As well as the museum or in the more obvious spots like the gate of the city wall, there can be some surprising places you can find evidence of the Etruscans. Debora loves to take people on her tours inside certain shops. A seemingly modern shop can hide some Etruscan or Roman secrets of how people lived
  6. For fans of Under the Tuscan Sun, there are a few things that are good to know ahead of time. The fountain in the movie, seen on Piazza Signorelli, does not exist, and Bramasole, the villa from the movie is a private home and cannot be visited. You can stop in front of the gate and take a picture, you can peek at the big garden and the facade of the building, but you cannot go inside
  7. Cortona, mostly due to the book and movie, is very touristy compared to the surrounding areas, but it’s also popular because people that go there, perhaps because of Under the Tuscan Sun, tend to fall in love with it and recommend it to others. The city has lots to offer – lots of art, history, painting, and water coloring, making the most of the amazing landscapes. And it’s not simply a tourist town, it is somewhere that has mostly locals living, working, shopping, and eating. This means that generally the quality of food in Cortona, even if it’s a touristy place is very high
  8. Specialties in the area include the white cow, la Chianina. Aglione means big garlic, the taste is much sweeter than traditional garlic – you don’t have that strong taste (or the breath to go with it). It’s often found with pici type of pasta, in a tomato sauce. or something with aglione. All’aglione is this tomato sauce with this garlic. Cortona is also famous for the Syrah wine variety so you will find that all over the city
  9. One of the iconic things when you drive around this landscape, and of course an important part of the food culture, are the large, majestic, white Chiana cows. These are the cows whose meat is used for bistecca alla fiorentina, but they do it a little bit differently in the valley. It will often be a delicious ragu. When you eat it – you immediately understand the quality
  10. The small town of Castiglion Fiorentino can be found between Cortona and Arezzo. Again dating back to Etruscan times, the historical center has the main gate and the streets are straight out of the Middle Ages. In the main square, in front of the city wall, you have a lodge (which in Italy means an open gallery – a kind of covered corrido) called Lodge Vasellani which is where artist Giorgio Vasari worked
  11. For a while in the past this lodge was closed and was used only used as a market, but in the 18th century, three arches were opened and are like big windows over the Val di Chio, another valley
  12. Castiglion Fiorentino is one of the most important villages in the area due to its river. There is a castle is a symbol of the village and can be seen from all directions as you approach Castiglion Fiorentino 
  13. The horse race, the Palio dei Rioni, is held on the third Sunday in June and all the week before the Palio is a celebration in Castiglion. There is music, historical processions, with people dressed as knights, and other medieval characters. The day before the race there is the pre-dinner there all the people from the district teams meet to support for their district. Then on the Sunday, the Palio is a big race in the square
  14. The village has transformed in the medieval style – the colors, the costumes, flags, coats of arms, food and the market all mean you can experience the Middle Ages in our modern time
  15. Over Ferragosto, the Italian public holiday on the 15th August, there is a vintage festival in Castiglion Fiorentino. Celebrating all things 50s – old cars,  Vespas, dresses and rock, and roll music
  16. Lucignano, known as the pearl of Val di Chiana,  is a very small town, but it’s special and unique for a couple of reasons. Firstly, it is laid out in an elliptical, ring-like shape. Secondly, in its museum it has L’albero d’oro , the Golden Tree. This is a piece of ancient metal art decorated with coral crystals, made from golden, copper and silver. It is also know as the L’albero dell’amore, the Tree of Love and it’s a tradition that engaged couples visit the tree to be blessed with eternal love for their marriage. Lastly, the vibe of Lucignano, which is pretty quiet, with just a few restaurants or cafes – but is representative of a really authentic Tuscan and Aretino atmosphere and spirit
  17. Lucignano is also known for La Maggiolata, a parade of floats covered in flowers. In the last two weekends in May, all Lucignano, the balcony, the alley, the arches – everywhere is decorated with flowers. The predominant flowers are the yellow La ginestre flowers. The parade runs along the main street and there’s music from folk groups, and they have medieval games. The floats are decorated with unbelievable flower construction – which might be a representation of a giant bottle of wine or there are all ladies decorated with flowers. There is color everywhere, with the street covered in flowers and petals that fall from the floats and the smell is divine
  18. The area of Val di Chiana is the perfect place to stay in an agriturismi or for villa, not only for the wonderful surrounding landscape but as it has such great access to so many things – gorgeous towns and villages and wineries. There are very few hotels in the area and most agriturismi or B&B you would find in a typical, local village, likely in an 18th-century, character-filled building, or a villa where you can live the Under the Tuscan Sun life for a week. Not only is it great to explore this beautiful corner of Tuscany, but you can quickly get to Montepulciano and other parts of Tuscany, to Umbria (in fact from Castiglion Fiorentino you can see Umbri’a’s Lake Trasimeno, the wonderful, historic city of Gubbio is not far away and you can also reach the Marche region easily

About our guest – 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

  • Cortona – beautiful Tuscan town, made famous by Frances Mayes memoir and the film Under the Tuscan Sun
  • Val di Chiana – the beautiful valley surrounding Cortona
  • Rugapiana – the main street of Cortona (formerly known as Via Nazionale)
  • Piazza Signorelli, Piazza della Repubblica and Piazza Garibaldi – squares in Cortona
  • Castiglion Fiorentino – village between Cortona and Arezzo
  • Val di Chio – valley just outside Castiglion Fiorentino
  • MAEC, the Etruscan Academy Museum – museum in Cortona, with history dating from the Etruscan time up to the 20th century
  • Lucignano – small Tuscan town, built in an elliptical shape. Known as the “pearl of Valdichiana”
  • The Golden Tree  – in the town’s museum, a unique masterpiece of the goldsmith’s art from the Gothic period which is a lucky charm for lovers
  • Val d’Orcia – a region of Tuscany, central Italy, which extends from the hills south of Siena to Monte Amiata
  • Lake Trasimeno – lake in Umbria on the border of Tuscany

Food & Drink

  • Chianina – the white cattle breed from which they make bistecca alla fiorentina found around the area of Manciano, Castiglion Fiorentino
  • aglione –  means “big garlic“, the garlic typical of the region with a sweet taste
  • pici all’aglione –  Tuscan hand-rolled pasta with tomato and garlic sauce
  • Syrah – Cortona is famous for this wine (also known as Shiraz)


  • Chimera of Arezzo – bronze statue of the Chimera, “she-goat” – a monstrous, fire-breathing hybrid creature
  • Under the Tuscan Sun – book by Francis Mayes, turned into a movie
  • Bramasole – the house she buys and renovates in Under the Tuscan Sun
  • Etruscan civilization – civilization of Italy, with the earliest evidence of a culture dating from about 900 BC
  • Giorgio Vasari – an Italian painter, architect, engineer, writer, and historian
  • Ferragosto – yearly celebrations and public holiday in Italy on 15th August
  • flux capacitor – what Marty McFly used to go back in time (and to the future) in the Back to the Future movies of the 80s
  • La Maggiolata – flower festival in Lucignano in May
  • ginestre – the yellow flower most predominant in the flower decorations
  • Joust of the Saracen & Archidado Joust – medieval jousting events in Arezzo and Cortona

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