The town of Sestino, as well as the town of Badia Tedalda, is the only Tuscan municipality in the Montefeltro area. It is set in the province of Arezzo at 458 m of altitude. It is rich in rural areas, such as San Donato, Monteromano, Petrella and Monterone. In the latter centre, the parish of San Pancrazio can be visited.

Originally, Sestino was a "oppidum", a big Roman fortified village. The evidences of this time are traceable in numerous findings exposed inside the town's national archaeological museum. There are findings going from the IX century B.C. to the IV century A.D., such as marble and stone statues and the remains of a funeral small temple made in the post-Augustan era.
Under the Romans, Sestino was also the defensive base of the pass between the Romagna region and Tuscany, at the time of the Punic Wars. With the fall of the Empire, Sestino became part of the Byzantine Exarchate.
An imperial document written by Otto I in 962 certifies the concession of Sestino and its territories to the Carpegna family. The town, that had been included in the diocese of Montefeltro after the year 1000, progressively became a direct dominion of the Church, which was definitively sanctioned in the XIII century with the concession of Sestino as a vicariate to Dadeo da Casteldelci, an ancestor of Uguccione della Faggiola's who was loyal to the Pope. His dynasty, that the Malatesta later substituted, governed the town until 1371.
Federico da Montefeltro conquered the town in the XV century, and it entered the Dukedom of Urbino. Yet, the Pope's influence on the town did not stop. In 1516, Leo X, Lorenzo The Magnificent's son, settled that the Dukedom of Urbino was ruled by another member of the Medici family who was called Lorenzo, as well.
As a consequence, a harsh fight between him and Francesco Maria della Rovere, who was Urbino's previous duke, set off and it ended with the victory of the Florentine militia and the annexation of Sestino to the Tuscan Grand Duchy in 1520. Sestino followed the fate of the Grand Duchy as a town hall and as the seat of a vicariate, until its annexation to the Kingdom of Italy in 1860.