Sestino is the easternmost town of the province of Arezzo and of the entire Tuscany, even though it is geographically part of Foglia, a valley of the Marche region.

Etruscans, Umbrians and Sénon Gauls used to live in the area of Sestino, which in the 1st century B.C. became a roman municipality called Sestinum. After the fall of the Western Roman Empire, it continued to be under Byzantine’s influence and became part of the “Pentapoli Annonaria”. In the Middle Ages Sestino became part of the religious province of Massa Trabaria. From 1371 until 1465 the Malatesta family from Rimini owned these lands, then Sestino became a vicariate jurisdiction thanks to pope Paolo II. In 1520 pope Leone X took possession of Sestino and in 1575 he assigned to the city the role of “capitanato di giustizia”. Until 1779 Sestino was a “piviere nullius diocesis”, a religious jurisdiction with independence from nearby dioceses, but under direct control of Papal States.

Garibaldi square is the heart of the village; here lies the Town Hall that, in its basement, has got barrel vault rooms of the 14th century. Nearby, in Martiri Square, there’s the Municipal Theatre “Pilade Cavallini”, built in the 19th century.

The parish church of st. Pancrazio, is the most important religious site of the town. It was built in the 9th-10th century on the top of the ruins of some religious buildings of the Augustan period.

The church of Our Lady of Mercy (Chiesa di Santa Maria della Misericordia) was built in the 16th century and was owned by the confraternity of the same name, which used to manage a hospital and had a convent of Augustinian nuns. It was restructured in 1766.

The major interesting place in Sestino is its precious National Antiquarium, an archeological museum divided in two parts which retraces the history of the roman municipality period of the city.

The part of the museum dedicated to epigraphic monuments hosts a very important collection of dedicatory and funerary inscriptions. There are also numerous statues and bas-reliefs; the most importants are a statue of Aphrodite, a head of Augusto, a young man statue and a splendid funerary monument in Hellenistic style.

The surroundings of Sestino are full of treasures, too. Many hamlets can be found in the area, such as Montenerone, where in the past a customs branch was located, and it is considered to be one of the most well-preserved fortified villages of eastern Tuscany.

In the locality of Casale there is the church of st. Michele, built on the ruins of a Roman building; its mid-circular apse has decorations in high relief of the 12th century. In Castello, another locality of the area, there is an impressive Tower of the 11th century and the church of st. Donato, of mediaeval origins which was restructured many times. In the hamlet San Gianni there’s the church of st. Gianni in Vecchio, built on the ruins of an early middle ages building. It hosts high reliefs with allegorical figures of the 12th century.

The symbol of the area is the Rock of Simone (Sasso di Simone), at the centre of the natural reserve of the same name which is divided between the Province of Arezzo and Pesaro Urbino. It is a big calcareous rock shaped like a regular parallelepiped, 1.204 metres high, which rises above the Apennine mountains surrounded by beautiful natural landscapes.

According to the legend, the Rock of Simone takes its name from the hermit who dwelled there. The place was chosen by Cosimo I de’ Medici in 1565 to build a so-called City of the Sun, a fortress-town which could be used as a defence of the eastern borders of the Granducato di Toscana. The project was assigned to Giovanni Camerini e Simone Genga, but at the end of the 1600s the project was put aside and nature regained those lands. Of that idealistic project of the Medici family, now there are only some ruins left that can be seen.

Sasso di Simone e Simoncello Nature Reserve