The walls of Montefollonico date back to the end of the 13th Century. They were demolished and re-built several times during the wars between Siena and Florence, between the 13th and 15th centuries, when Montefollonico was allied with Siena. Its bitter enemy and neighbour Montepulciano was allied with Florence. Montefollonico once gave asylum to Ghibelline exiles from Siena, in thanks for which the Republic of Siena paid “masters of stone and timber” to construct several lengths of the village’s walls. In 1400 the walls were strengthened by doubling them in the area to the northeast, from the Church of Saint Leonard round to the Triano Gate. There were 11 towers defending the walls. Once the wars were over, the walls were rebuilt to keep the population of Montefollonico (and the Republic of Siena) safe from any hostile assaults.