Monticchiello is a small medieval town located halfway between Pienza and Montepulciano along a secondary road that joins the two locations. The town which is located at an altitude of 546 meters is still today partly surrounded by the ancient walls of the XIII century. The small village of Monticchiello is immersed in the beautiful hilly landscape of the Val d’Orcia. But the main attraction of this village is above all the characteristic stretch of road with curves flanked by cypresses which is one of the most famous photographs of the Tuscan landscape typical of the Val d’Orcia.
The origin of Monticchiello is dated to the 10th century, in fact the name of the town appears for the first time in a document of that era. The town was controlled by the Republic of Siena for several hundred years. But at the end of the fourteenth century it was conquered by Florence, which a few years later returned the conquered village to Siena.
In the 16th century Monticchiello was the scene of bitter battles between Siena and its enemies. Then in 1502 it was conquered by Cesare Borgia, then in 1553 it was occupied by the troops of Charles V who destroyed the defensive works of the castle. The Sienese regained possession of it shortly after and refortified it, but in 1559 Monticchiello was definitively ceded to Florence.
In Monticchiello, part of the ancient walls with towers and the thirteenth-century keep are still visible today. The medieval village is accessed through the main door. The village is made up of old houses and narrow, twisted streets. There is an interesting 13th century church with a Romanesque-Gothic facade dedicated to Saints Leonardo and Christopher. Externally, the church has a facade with an ogival portal and a beautiful rose window, while inside, both on the walls and in the presbytery, there are interesting frescoes of the Sienese school of the fourteenth century. Finally, during the Second World War, in 1944, the town was the scene of a bitter battle between partisans and fascists.