Pienza and Montepulciano

Pienza and Montepulciano are part of Val d’Orcia one of the most beautiful regions of Tuscany. The Orcia region, located south of Siena (about half an hour away) combines in a small territory a great variety of attractions that have made the area to be included in the UNESCO World Heritage of Humanity.


Pienza Cathedral
Pienza Cathedral


Pienza is close to the Cassia state road and to important towns in the valley such as San Quirico d’Orcia, Castiglione d’Orcia, Montalcino and Montepulciano. It enjoys a very strategic location, on a hill overlooking the entire Val d’Orcia, with a splendid view. What was once a medieval village was transformed in the Renaissance into an ideal city due to the will of a single man. Not every small town has the good fortune to be the birthplace of a Holy Pontiff.


Where to eat? I recommend Trattoria latte di Luna, Sette di vino (always so busy especially in summer), and Baccus Osteria.

The most important things to see in Pienza are listed in this list of the TOP must-see places in Pienza:

  • Piazza Pio II
  • Pienza Cathedral
  • Palazzo Piccolomini
  • Civic Palace
  • Corso Rossellino


Palazzo Piccolomini
Palazzo Piccolomini


Monticchiello is one of the many beautiful scenic towns that you can visit when traveling in the Tuscan province of Siena. The origins of the town date back to Roman times, and in the mid-13th century, it became a medieval fortress. Today, the town is noted for its strong community spirit, summer theatrical productions, and farmhouse tourism. It’s a very little village but you can make a stop because is located between Pienza and Montepulciano.


Originally this city was an Etruscan fortress over which Florence and Siena fought during the Middle Ages. The Duke of Tuscany gave the order to rebuild the city and protect it with new walls, whose responsibility fell on the architect Antonio da Sangallo.

The medieval character and its elevation on a hill make it particularly beautiful for the panoramic view. Below, we will give you more details about this interesting place. Montepulciano enjoys international recognition for its exquisite red wines, among which the Vino Nobile di Montepulciano stands out.

Traffic in Montepulciano is restricted, so the tour is done on foot. You must leave your car in one of the many parking lots that are well marked.

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