Why Castiglion Fiorentino

  • Good living
  • Surrounded by greenery
  • Peace and relax
  • Various little village
  • Good food and wine
The territory of Arezzo is very wide and varied, ranging from the plain that opens onto the Val di Chiana and the Arno, to the hills, south of the city, to mountainous areas, especially in the eastern part. Let's see the main municipalities together :)
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There is so much to see, do and enjoy in the Province of Arezzo, a land that is rich both from a cultural-artistic and food and wine point of view. There are 37 municipalities that are part of the province of Arezzo, tourist, and holiday destinations.

Here we report only those that we have visited and that deserves a visit 😙


Anghiari is a beautiful village that dominates the upper valley of the Tiber river (Valtiberina) and the Sovara stream. The powerful city walls give the town a truly medieval aspect.

The historic center is characterized by Renaissance palaces, picturesque stone houses, narrow alleys. The numerous religious buildings consist of small churches, many of which date back to the Middle Ages. Traditional activities are the restoration of furniture and crafts, mainly firearms, wicker baskets, wood, and wrought iron. Also, it is full of small artisan shops, among which those of ceramics, decorations, and fabrics stand out. There are also numerous antique dealers, all supported by skilled restorers.

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In the surrounding area, there are numerous well-preserved castles 🏰 such as those of Sorci, Montauro, and Galbino full of ghost legends 👻.

For a visit, it is advisable to start from Piazza Baldaccio, the connecting point between the first inhabited settlement and the medieval village.

Going along via della Prepositura you reach Piazza del Popolo where two main buildings stand out. The Palazzo Pretorio dates back to the 14th century but was remodeled a hundred years later. On the facade hang the coats of arms of the vicars and commissioners who succeeded the government. On the southern side, there is the bulk of the Cassero.

Going along the alley of the Piazzola you reach La Badia. The first place of worship in the village.

Through Porta S. Angelo you enter the ramparts of the walls, from where you can enjoy an excellent view of the Tiber valley and up to Sansepolcro. At the center of the district is Piazza Mameli, all surrounded by 15th-century buildings including Palazzo Taglieschi, the composite Palazzo Testi, and the church of S. Agostino.

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The town has been awarded the “Orange Flag” 🚩 award confirming the excellent quality of tourist accommodation. It is also among the “most beautiful villages in Italy” 🌍.


The territory of Castiglion Fiorentino extends over a border area between Tuscany and Umbria. The historic center of the town, dominated by the keep tower and surrounded by walls, has maintained the typical medieval layout and contains historical and artistic architecture.

Castiglion Fiorentino allows you to overlook the splendid views both towards the Val di Chio and towards the Preappennino.

The panorama is dominated by the castle of Montecchio 🏯, which was the home of the famous captain of fortune John Hawkwood. The historic center offers a suggestive view of the medieval period with the walls, the doors, the Cassero tower, the church of S. Angelo, the church of S. Francesco, the church of S. Agostino, and the Palazzo Pretorio. In the following period (Renaissance) the Vasari loggia was erected in Piazza del Comune, the church of the Gesù, and the church of the Consolazione. Those who visit the area in the third week of June will be able to attend the famous “Palio dei Rioni”, an equestrian competition between the city districts of medieval origin that takes place in the historic center of the city.

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Castiglion Fiorentino was awarded the “Orange Flag” 🚩 award for the level of conservation of the historical and artistic heritage and the environment and for the tourist reception.

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Cortona, which was originally an important Etruscan city, has maintained a prominent position in the artistic and cultural fields in the following centuries. With the exception of some buildings from the Renaissance period, the appearance of the town is decidedly medieval, with the center full of small narrow and suggestive streets. It is currently the main tourist and cultural attraction of Valdichiana.

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The main points of attraction are the Girifalco Fortress, the Franciscan Convent and Hermitage Le Celle and the Museum of the Etruscan Academy and the City of Cortona, and the Diocesan Museum. Important events are held periodically in the town, such as the Cortona Antiquaria exhibition-market, the Giostra dell’Archidado 🎠 , and the Cortona On the Move festival.

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The film “Under Tuscany sun” was set in Cortona 📽, inspired by the move to the outskirts of the town of the American writer Frances Mayes, author of the successful novel of the same name.


The territory of Loro Ciuffenna, dotted with abbeys, parish churches, and ruins of castles, is all lying on the southwestern portion of Mount Pratomagno. The whole area is green with woods and agricultural crops and you can enjoy an excellent view of the upper Arno Valley (Valdarno Superiore).

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A village suspended over a stream, characterized by a suggestive intertwining of narrow streets and alleys paved in stone. Nearby, the splendid Pieve di Gropina, one of the most significant examples of Romanesque architecture in Tuscany, and the small and picturesque village Il Borro, where numerous artisan shops have been installed, are worthy of note.

Among the monuments and places to visit in Loro Ciuffenna is certainly the Mill of the Miller, built around the year 1100, located on a cliff overlooking the Ciuffenna stream. It is the oldest watermill in all of Tuscany, although it is currently used only for grinding chestnuts, a typical product of the area.

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Monte San Savino is an ancient village full of medieval and Renaissance suggestions.

The village is also known for the ceramics that skilled artisans forge daily still today in their workshops, using ancient techniques handed down from generation to generation.

Another strong point of the town is gastronomy, where you can eat the traditional porchetta with herbs and drink fine wines 🍷.

It is the homeland of the great Renaissance sculptor Andrea Contucci known as Sansovino and of Pope Julius III.

The historic center develops from the Cassero, an ancient fortress of the fourteenth century, then along Corso Sangallo, flanked by the Renaissance Logge dei Mercanti, today the seat of the Municipality, from Palazzo Pretorio with its Tower, from the Pieve and the church of Sant’Agostino which houses a beautiful Assumption by Giorgio Vasari. A particular summer event is the Popular Theater Review “Il Giogo” which takes place every year in Montagnano, in the month of July.

Nearby there is the Castle of Gargonza 🏰, which we absolutely recommend seeing.

The castle, dating back to the 12th century, was owned by the Ubertini family. Within the walls, there are eighteen peasant-type dwellings, called “houses“, each with a particular name 🏡: Casa Nicolina, Casa Nerina etc … The houses are intended for tourists. The structure is also used for conferences and business meetings.


Sansepolcro is the most populous center as well as the administrative capital of the Tuscan Valtiberina. Initially a free municipality and then the cradle of Renaissance culture, it is an important point of reference and integration at the intersection of three regions: Marche, Tuscany, Umbria. Numerous personalities were born in the town, especially in the fields of art and science: the Renaissance painters Cherubino Alberti, Raffaellino del Colle, Matteo di Giovanni, and Piero della Francesca, the mathematician Luca Pacioli, a friend of Leonardo da Vinci.

In the town, there are numerous churches ⛪ works by important painters of the Renaissance and Mannerism, such as Perugino, Rosso Fiorentino, Luca Signorelli, and others, many of which are exhibited in the Civic Museum. Of note are the unusual Stained Glass Museum and the Aboca Museum botanical-pharmaceutical museum.


Poppi is a village of medieval origins, located in the northernmost part of the Casentino, and one of the rare “walled cities” that has remained almost intact in its artistic beauties. The historic center deserves a careful visit, for the architecture of the buildings, the characteristic districts with the streets lined with arcades, and the narrow side alleys. From Porta Fronzola, the entrance to the town, you can already see the Tower of the Devils at the top 👿, the epilogue of the story of Countess Madelda.

The village is an excellent panoramic point of the entire northern Casentino: you can admire the ridge of the Pratomagno, the high course of the Arno river, and the wide relief of the Apennines, from Monte Falterona to the rocky spire of La Verna. The territory also includes the complex of Camaldoli and the welcoming town of Badia Prataglia, both surrounded by the National Park of the Casentinesi Forests ⛺.

It is all perched on a hilly relief overlooking the Arno River and surrounded by 13th-century walls. Here you will find the castle of the Guidi counts, Piazza Amerighi, and the Abbey of S. Fedele and is crossed by the main road (via Cavour) flanked by elegant buildings and arcades. Piazza Amerighi, from where you can observe an excellent view of the surrounding area, is dominated by the Madonna del Morbo church. At the bottom of the Pratello, the first residence of the Guidi counts remained. Behind the castle is the Church of the Agostiniane ⛪ which, on the facade, has a terracotta by the students of Andrea della Robbia, while the one inside is probably the work of Benedetto Buglioni.

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The Castle of Poppi 🏯 is one of the best-preserved castles in Tuscany because it has not undergone major changes over the centuries. Inside there is the Museum of the Battle of Campaldino, which exhibits a reduced-scale reproduction of the event with 3,000 miniature toy soldiers. The other rooms of the structure are used for conferences, art exhibitions, and, in the summer, for concerts and theatrical performances.

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The castle, besides having obviously been the scene of blood and fights, welcomes a legend that fascinates and makes people discuss 👻. It is said that the ghost of the cruel Countess Matelda still wanders in the castle of Poppi: the beautiful Countess Matelda received a different lover in her rooms almost every evening. After consuming, to prevent her lovers from revealing her secret, she made them fall into a ditch where there were sharp blades waiting for them or men who tortured them until her death. One day, however, the women of the village rebelled against this situation, seeing many local men mysteriously disappear. So they decided to wall the Countess Matelda alive in the tower renamed Tower of the devils. Even now here are those who swear to sense the presence of the countess who on some nights she wanders around the castle in search of men to conquer. Other legends make Poppi Castle even more mysterious and fascinating. There are those who say, that on nights of a full moon 🌕 in the courtyard of the castle, where in the past duels were fought and dead fighters were buried, the noises of weapons can still be heard.

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The municipality is the result of the merger of two inhabited centers that have had considerable importance in the past, both for the history that united them and for the textile industry. In fact, the economic resources came essentially from the production of woolen cloth for clothing and for domestic use. The history of both locations has always been combined with the beauty of the lush woods and the majesty of Mount Falterona and it is no coincidence that the offices of the Casentinesi Forest National Park are located here.

The municipality of Pratovecchio Stia is currently also a “Slow City“, that is, the city of good living 🤗. The geographical position allows easy access to that still uncontaminated area of ​​the Casentino which contains important natural habitats. Currently, quality agri-food products and tourism constitute the main economic resource.

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Stia in Casentino is the first town crossed by the Arno river, which originates from Monte Falterona. You can find many places to discover, below the list:

  • The Palagio Fiorentino.

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  • The Park Planetarium
  • The Castle of Porciano and its village
  • The Castle of Romena

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  • The museum of the art of wool
  • The ski and mountain museum
  • The parish church of Santa Maria Assunta in piazza Tanucci
  • Adrenalina Casentino Adventure Park, to have fun in the midst of Nature
  • The waterfall of the river near the Ospitale dei Brilli.

We love these territories very much because they are surrounded by greenery. We are sure you would like it too 😍.

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Other posts of the trip: Discovery Arezzo

Post Author: wildcouple95 |

We are Alessia & Luca. From Tuscany with love ♥ Passionate about travel, photography, nature, sports and trekking. Fall in love with our Italy, with its beautiful crystal clear waters and high mountains, but we don't miss opportunities to travel abroad. Let's travel together!

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