Montemassi Castle

The magnificent Montemassi Castle has been disputed for centuries. And when you see it, you can understand why.

The 11th-century castle shaped the village for centuries, ensuring that it retained its iconic pinecone shape.

The castle has recently been restored and opened to tourists. It is worth the 18-minute drive from Roccastrada.

The Sienese conquered Montemassi as early as 1260, but left the town in the hands of local (and presumably loyal) counts. After becoming rich thanks to the Italian condottiero (warlord) and duke of Lucca, Castruccio Castracani, the city decided to rise up against Siena.

It did not work so well. The Republic of Siena invaded and brought Montemassi back into control in 1328.

The painting above was commissioned to celebrate the victory. He is actually very famous. It is by Simone Martini and is on display in the Palazzo Pubblico in Siena. It depicts a rider on a bright white horse.