The history of the municipality of Pienza, which is in the province of Siena at 492 m asl of altitude, is strictly linked to the figure of the Pope Pius II, who was born in this little town and who transformed it in a wonderful Renaissance city once he sat on the papal throne.

The first settlement of the territory is a "curtis" called Corsignano of which the first information dates back to the IX century.
Nevertheless, the ancient parish of Corsignano, which can be still visited today, could even be dated to a century before and that is why it can be considered the core of the first built-up area. Until the XII century, this area was property of the St. Salvatore Abbey, which benefited from the concessions given by emperors. Later, the authority of Siena was established on the Corsignano territory.
During the years, the Republic of Siena was obliged to deploy a conspicuous military garrison across the area to face the constant attacks by Orvieto and Florence, the cities which occupied the village for some years in the XIII century.
In 1330, Corsignano became a town hall and a vicariate one century after. In the meantime, the property-owning Piccolomini family was establishing its presence over the village. Enea Silvio, the future Pope Pius II, was born in this family in 1405.
In 1458, Enea Silvio Piccolomini became pontiff and he immediately started the reconstruction of his home town, which was re-founded with the name of Pienza.
The embellishment project of the ancient village was assigned to Bernardo Gambarelli, called the "Rossellino", whose some XV-century buildings are still visible today as well as the Piazza Pio II, designed by the architect himself. This square, which is the pivot of the city, is also the place overlooked by the Assunta's Cathedral and the most imposing buildings. For a weird of fate, both the Pope and the architect died in 1464, without the possibility to fully enjoy the fruit of their labours.
In the XVI century, Pienza became a rich and lively economic centre, therefore becoming the target of some commanders of mercenary troops and some Tuscan military forces. For instance, in 1502, the city was pillaged by Cesare Borgia, while other damaging stemmed from the conflict between Siena and Florence at the half of the century. In 1559, Pienza became part of the Medicis' s Grand Duchy, thanks to which the city lived a period of a renewed political and economical stability.
The Castle of Monticchiello can be also admired near Pienza. Despite its medieval origin, this stronghold marked the final history chapter of the city.
In effect, in 1944 it was the setting of a harsh conflict between the Partisans and the Nazi groups. Also thanks to the aid given by the population, the firsts scored one of the most significant military victories of the Tuscan Resistance.