10 small towns to visit near Arezzo

In this post we’ll explore 10 small towns in the Arezzo surroundings: which one is your favorite?

1. Cortona

Cortona is a charming town located in the Valdichiana Valley at 30 kilometres from Arezzo and well known for being the set of the bestseller “Under the Tuscan Sun” by Frances Mayes. The city, enclosed by stone walls dating back to Etruscan and Roman times, boasts interesting places to visit as well as wonderful views of the Trasimeno Lake.

You can begin your tour of the town in Piazza della Repubblica and Piazza Signorelli, once a unique site of an ancient Etruscan-Roman forum. All around there are medieval buildings such as the Palazzo Comunale (Town Hall), which dates back to 1236; the fourteenth century Palazzo del Capitaino Popolo, Palazzo Pretorio, and Palazzo Casali, which houses a museum; the municipal and Accademia Etrusca’s library; the town’s historical archives, the Museum of the Etruscan Academy and the Museum of the city of Cortona. You can also visit the monumental complex of San Francesco that includes the church and the convent, and if you continue up you can reach the upper part of the town with its narrow streets and medieval buildings.


2. Sansepolcro

Sansepolcro is the main town in the Valtiberina area, located at about 37 kilometres from Arezzo. You can start your visit from the Cathedral of Saint John, a Catholic church founded 1000 years ago with a great historical value. Here is where Saint Francis of Assisi preached in 1211 or 1212, and also where Piero della Francesca worked in the church. Then you can visit the Sansepolcro Civic Museum that houses a number of artworks, including notable works related to the figure of Piero della Francesca and the Della Robbia’s art.

Sansepolcro has many churches, but the church of San Lorenzo deserves a special mention because of the masterpiece of Mannerist paintings that it houses, “The Lamentation over the Dead Christ” by Rosso Fiorentino (1528), which is on the main altar. The best period to visit Sansepolcro is during its ‘Palio della Balestra’ and its Flag-games.


3. Anghiari

Anghiari is a medieval hill town situated in the Valtiberina, at just 30 kilometres from Arezzo, characterised by windy streets and stone houses decorated with flowers. It is considered one of the “most beautiful villages in Italy” and received the Orange Flag by Italian Touring. This small village is enclosed in massive 13th century walls with perfectly preserved corners and architectures. You can visit the “Cassero,” the monastery of St. Bartholomew, the apse of the Church of St. Augustine and the Bastione del Vicario. The perfect period to visit is during the Mostra-Mercato dell’Artigianato della Valtiberina (the Handicraft Market of the Tiber Valley) held in late April and early May.


4. Foiano della Chiana

Foiano della Chiana is located 32 kilometres south of Arezzo, on the border with the province of Siena. In the past, Foiano was the best defence point in the Valdichiana because it was surrounded on three sides by marshland. Leonardo da Vinci was called to draw up plans for the draining of the Valdichiana. Foiano della Chiana is surrounded by city walls and from the gate a road leads to Piazza Cavour where Palazzo Comunale faces the Palazzo Monte Pio. Inside Foiano you find notable works by Andrea della Robbia as well as other artists of the Renaissance. You can walk on Corso Vittorio Emanuele and see the eighteenth century loggia and Piazza della Collegiata, the church of San Michele Arcangelo, the church of Santa Maria della Fraternità, the 14th century Palazzo Pretorio, and much more.

The best period to visit Foiano della Chiana is in February during the Carnival. In fact, this is the most ancient carnival in Italy (since 1539), and Carnival floats are built throughout the year.


5. Lucignano

Lucignano is a small medieval hill town overlooking the Valdichiana and located about 25 kilometres southwest of Arezzo. Here you can visit the fortress, the sanctuary of the Madonna della Querce attributed to the Vasari, the convent of the Cappuccini, the churches of Misericordia and della Collegiata.

But Lucignano is particularly known for being home to the “Tree of Love” or “Tree of Life,” a 2,60 meter-tall Gothic masterpiece decorated with coral, enamel and rock crystal. People believed that the tree had a magic ability to make love last, so lovers would go there to make their promises of fidelity.


6. Castiglion Fiorentino

Castiglion Fiorentino is a walled city located just 18 kilometres from Arezzo. The area of Castiglion Fiorentino was inhabited in very remote ages, but an important settlement was developed in the Etruscan period, between the fifth and the fourth centuries BC. An Etruscan city wall has been found underneath the current Piazzale del Cassero, as well as the remains of an Etruscan temple under Sant’Angelo, one of the town’s churches. The city walls, including the main entrance to the town’s historical centre Porta Fiorentina, were erected in the 13th century.

Castiglion Fiorentino is renowned for the Etruscan archaeological site and for the nine-arch loggia in Piazza del Comune overlooking the valley, constructed by Vasari in 1513. The Cassero, which is the town’s fortress, was used as a convent and then as a prison. You can visit Castiglion Fiorentino during the famous “Palio dei Rioni” on the third Sunday of June, a horse race around Piazza Garibaldi, including a display of the ancient custom of flag-waving.


7. Chiusi della Verna

Chiusi della Verna is a municipality located about 25 kilometres north of Arezzo in the Casentinesi Forests National Park, between the valley of the river Arno and the river Tereve, in a strategic position between Casentino and Valtiberina. It is particularly known for the Sanctuary of San Francesco alla Verna, one of the most important Franciscan sanctuaries in the world, located on the Monte Penna and surrounded by beech forests. The sanctuary includes the small church of Santa Maria degli Angeli, the corridor and the Chapel of the Holy Stigmata and the Basilica dedicated to Santa Maria Assunta. You can also sleep in the monastery.


8. Poppi

Poppi is an ancient medieval village located in the Casentino area, at about 40 kilometres from Arezzo. It was mentioned as one of the most beautiful towns in Italy (I Borghi più belli d’Italia) since it is a perfectly preserved walled town. Within the things to see in Poppi there is the medieval castle of the Guidi Counts (known also as Poppi Castle) which dominates the surrounding countryside; the Church of Madonna del Morbo which is situated in the centre of the town and houses a painting of the Virgin Mary attributed to Filippino Lippi; the S. Fedele Abbey with valuable works of art. The historic centre of Poppi deserves a visit for the architecture of its buildings, its elegant arcades and its narrow alleys


9. Loro Ciuffenna

Loro Ciuffenna is a charming village rich in history and medieval military architecture located about 25 kilometres northwest of Arezzo. A beautiful single-arched Romanesque bridge that passes over the gorges of a stream characterises it. Loro Ciuffenna’s surroundings are characterised by the mountains and the Balze (unusual rock formations of clay and sand). Porta dell’Orologio (the clock tower) is the entrance of the village and, together with a second door, form the rest of the old castle. Once here you can visit the church of Santa Maria Assunta and the old mills that produced chestnut flour.


10. Monte San Savino

Monte San Savino is an ancient village of the Valdichiana located at about 25 kilometres from Arezzo. It is one of the first urban settlements in Tuscany, originating around the year 1100. Sloping walls with four gates surround monte San Savino and some of the principal monuments are in piazza Gamurrini. You can visit the town museum in the castle, the Church of Saint Clare with a Sansovino’s work of art, the Cassero and the Loggia dei mercanti.