How to reach
Monticchiello rises in the council of Pienza, in province of Siena. It can be reached following the motorway A1 up to the exit of Valdichiana and following the indications for Pienza or in alternative 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 from 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 was often object of wars and assaults, destruction and occupations. In the years 1229-35 the town was destroyed by the Orvietani,then at the to end of the 1300 it was occupied first by the Florentine and then by the Montepulcianesi and suffered others 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 in 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 great part preserved, reinforced by towers of various dimensions and shapes. Seven are the towers that we can admire today, two rounded flanking the S.Agata Gate (the only main entrance, several postern can be seen on the walled circuit) and other five square towers located in various points on the walls.The village inside the fortifications has maintained intact its medieval characteristics and walking for its alleys is like 'breathing' Tuscan medieval life.