Town Walls and Rocca of Monticchiello

How to reach

Monticchiello rises in the council of Pienza, in the province of Siena. It can be reached by following the motorway A1 up to the exit of Valdichiana and following the indications for Pienza or, alternatively, from the Orcia valley, first following the road SS2 Cassia 'til the cross with the SS146 for S.Quirico D'Orcia.


The castle, or better walled town, of Monticchiello, fief of the local family of the Lambardi, was thickly strengthened by the Senesis at the end of the 12th century, when it became an important borderline fortress. Monticchiello was the main center of the defensive organization on the oriental border of Siena and so during its history, it was often the object of wars, assaults, destruction, and occupations. In the years 1229–35, the town was destroyed by the Orvietani; then, at the end of 1300, it was occupied first by the Florentine and then by the Montepulcianesi, and suffered other serious devastation in 1553, founding itself on the road of the Imperial army during the 'War of Siena'.

The whole system of the fortifications is chained to the Rocca, set at the highest point of the hill where the hamlet rises. Only the mighty keep, built in 1260, with its bastioned walls endowed with machicoulis in stone (opening between corbels of the parapet through which the defenders can drop rocks or fire projectiles against an enemy directly below them) remains. The Rocca is private property

The town walls are instead, for the most part, preserved and reinforced by towers of various dimensions and shapes. Seven are the towers that we can admire today, two rounded towers flanking the S.Agata Gate (the only main entrance, several postern can be seen on the walled circuit) and the other five square towers located at various points on the walls.The village inside the fortifications has maintained intact its medieval characteristics, and walking through its alleys is like 'breathing' Tuscan medieval life.