The 11th century castle has shaped the town for centuries, ensuring that it kept its iconic pinecone shape.
The castle has been recently restored and opened to tourists. It's worth the 18-minute drive from Roccastrada.
The Sienese conquered Montemassi in as early as 1260, but left the town in the hands of local (and supposedly loyal) counts. After getting rich off the coattails of Italian condottiero (warlord) and duke of Lucca, Castruccio Castracani, the town decided to rise up against Siena.
It didn't work out so well. The Republic of Siena invaded and reined Montemassi back into control in 1328.
The above painting was commissioned to celebrate the victory. It's actually very famous. It is by Simone Martini and hangs in Siena's Palazzo Pubblico. It depicts a knight on a brilliant white horse.
Photo: Alienautic via Wikipedia Commons.