There were a few spots I found that I could overlook the Val di Chiana; the best of which was from Chiesa di Sant'Agostino or Church of Saint Augustine. From there, I enjoyed the stunning views of terracotta roofs, olive groves and vineyards. However, it did not surpass the Val d'Orcia I glanced over from the hilltop of Pienza.

And yet, Montepulciano has a lot more to see. I found the market square named the Piazza Grande small despite its name. And the next to it was the Palazzo Comunale that still functions as the town hall. Its shape looked just like the Palazzo Pubblico I saw in Siena or Pienza’s campanile. Perhaps, it was the design often used in the architecture of the Renaissance. Inside the Duomo, there are several masterpieces from the 15th century. Madonna del Pilastro by Sano di Pietro is one of which and this picture I saw at the Via del Poliziano, too.
Walking down the sloping street, I found the tin man ringing a bell on the top of the clock tower. They say it is a clownesque character called Pulcinella from the 16th century.