Scenic Itineraries in Valdorcia, the magic land south of Siena

Where to go in Tuscany, Italy

At the beginning of December I’ve passed some days in the wonderful Renaissance town of Montepulciano, in the province of Siena.
Montepulciano’s location is very strategic, it’s ideal to start countless itineraries to visit some of the most beautiful sights and attractions of Tuscany and Umbria: Montalcino, San Quirico d’Orcia, Bagno Vignoni, Pienza, Cortona, the beautiful Trasimeno Lake, and the magic Crete Senesi.

Well, we started our itinerary moving west of Montepulciano to reach the enchanting hill top town of Pienza, one of the main destinations in Val d’Orcia.

Pienza, stunning village with endless views near Siena

pienza in valdorcia

Holding a dominant position all over the valley, Pienza enjoys one the most vast and beautiful panorama of the area.

Located halfway between Montalcino and Montepulciano; Pienza takes its name from Pope Pius II, Enea Silvio Piccolomini, that was born here in 1405.
Enea was a great humanist and a true man of the Renaissance; when he became Pope, he transformed his childhood home in the village of Corsignano, in a true symbol of Italian Renaissance.
The project was followed by the architect Bernardo Rossellino, under the guidance of the great humanist and Renaissance theorist of art Leon Battista Alberti. In just 3 years Pienza became the Ideal City of the Renaissance, in a perfect harmony between nature and history.

The main square of the village, Piazza Pio II, is surrounded by historical palaces and buildings; on one side of the square there’s a beautiful and ancient well, known as the Well of the Dogs, il Pozzo dei Cani.

The Cathedral of Pienza, the Cattedrale dell’Assunta, whose tall and pointed bell tower is visible even from a far distance, hosts very fine paintings by the most renowned artists of the period.

You should absolutely visit the residence of the Pope, the majestic Palazzo Piccolimini, elegant Renaissance palace, whose courtyard leads to the fabulous hanging gardens and the Loggia that offers an outstanding panorama all over the Sienese countryside, a true spectacle!
No wonder that the famous Italian director Franco Zeffirelli shot some scenes of his famous movie “Romeo and Juliet” right within Palazzo Piccolimini.

I also recommend a visit to the Museo Diocesano, where you can admire fine artworks from the Sienese school and many beautiful paintings dating back to the 14th century.

After visiting museums, palaces, and after taking nice pictures of the town, we had lunch at our loved restaurant! The Osteria Baccus!

Needless to say that the food and wine were excellent as always; this time I tried the “Dolce dell’Osteria” (the osteria’s cake), a dream 🙂

We then left Pienza to move south, following the scenic road lined by cypress trees that winds up and down amidst scenic hills and a silent nature, leading to the fortified village of Monticchiello, whose extensive walls and fortress can be seen from a distance.

Monticchiello and the famous road lined by cypress trees


Once there, you’ll get vast and breathtaking views over Pienza and the magic landscapes all around. Passing under a huge and fortified medieval door, after a few steps we arrived in front of the little Church of Saints Leonardo and Cristoforo, dating back to the 12th century.

When I entered the church I was actually stuck and surprised by the beauty of the wonderful, though partly damaged 14th century frescoes, and by the splendid painting of a Madonna with the Child by Pietro Lorenzetti, a real masterpiece.

On the right of the church my attention was captured by a little shop selling a lot of beautiful locally handmade fabrics, what a pleasant surprise! It’s nam is “Tele Artigianali Fidia Cappelli” Well, when I get out of the shop, I had a lot of Christmas presents with me:-)

The name of Montichiello is also associated to the famous Teatro Povero (the poor men’s theater), whose theatrical representations started in 1967, featuring a play written and performed by the villagers to represent their local folk and farming traditions.

The play is put on stage during the last week of July ad the first week of August.

If you are looking for a very good restaurant in town, then stop at the restaurant la Taverna di Moranda to taste very exquisite local dishes!

Montichiello is a very tiny and less touristic village, but its atmosphere is unique; on a cold day of December we were the only ones going around, we enjoyed the silence and the amazing panorama we get from every corner.

If you are looking for unique hotels and accommodations near Pienza and Montichiello, read this post.

Well, on my next posts I will also tell you about San Quirico d’Orcia, Sant’Anna in Camprena, and many other Tuscan wonders…

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