The castle of Montepescali was first mentioned in a document in the XI century. Right at the entrance of the village is the Church of Santi Stefano and Lorenzo, in Romanesque style, documented since 1188. The wall on the left shows a fresco of the Sienese school representing Madonna Assunta (the Assumption of the Vergin, XIV century). In the presbytery is an altar made of stucco dating back to the end of the XV century and dedicated to San Sebastiano. Another church in Romanesque style is San Nicola Church, with a cycle of frescoes of the Sienese school (1389). Inside the Church is an altarpiece by Matteo di Giovanni depicting a portrait of the Virgin and Child seated on a throne surrounded by saints and angels (The Church is currently – March 2016 – under renovation) Other interesting sights in the city centre of Montepescali are public buildings and palaces. One can also walk along the town walls with their square towers: the tower known as Fortilizio di Guascone is the bigger one.