Monticchiello is a small centre in the heart of the Orcia valley whose beauty derives from its geographical position and the harmonious integration of its medieval architecture, and wide, well-proportioned spaces, which give the impression of moving around a large house. Closer examination will reveal many points of interest for the visitor, and we invite you to read our suggestions and proceed without hurry to appreciate the evidence of the town's past, and recent history. At a distance, Monticchiello appears simply as a tough, squat tower on the crest of a hill. The remains of its formidable walls and the medieval city gate are only visible to visitors when they are almost beneath the castle. Monticchiello was likely included in the list of castles, which Lamberto Aldobrandeschi ceded to the Badia Amiatina in 943. In 1156 however, it was given in feud to Pope Adrian IV by Count Paltonieri.
Despite the castle's name appearing in such ancient documents, the history of Monticchiello begins to acquire importance only at the beginning of the XIII century. The population, tired of the abuse of administrative power by the Teutonic Knights (who had obtained the castle in feud from the Church of Rome in recognition of their defence of holy sites) decided to side with the Republic of Siena, becoming its most faithful ally. The first document relating to the free Commune of Monticchiello is dated 1243. From this moment began the most flourishing and glorious period in the castle's history. With the completion of the keep, the walls and the church, crafts and commerce began to develop. Agriculture improved and the population increased, together with a sense of community and civic conscience. The Commune published its statutes in Italian, and the people took an active part in political life making their own voices heard through the "Council of one for each family".
Today, an heir to an ancient and long-remembered solidarity is the Teatro Povero, the 'Poor Theatre', a most impressive and clear sign of the town's vitality, and the people's capacity to rediscover and reaffirm themselves in a public space, confronting themes of great contemporary significance. Every year a new production, 'written, conceived and directed by the people of Monticchiello' returns to speak of past, present and future events of this community.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.
Monticchiello is part of Comune di Pienza, in the province of Siena. It can be reached following the motorway A1 up to the exit of Valdichiana and following the signs for Pienza or alternatively from the Val d'Orcia, first following the road SS2 Cassia until the crossing with the SS146 for S.Quirico d'Orcia.