Montemassi may not be in Toscana’s top travel listings but it is, nevertheless, a jewellery to be explored.
Originated as a fortified village it was first conquered by The Republic of Siena in the mid-13th century and then by the condottiero Guidoriccio da Fogliano. If you visit the Palazzo Pubblico of Siena, you will be able to see a most famous fresco depicting the event. In the mid-16th century after becoming part of the Grand Duchy of Tuscany, the city followed its history henceforth.
There is no ZTL imposed and parking space is usually not charged. Worth paying a visit if in the area – well maintained historical centre and amazing views over the countryside.