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  • Writer's pictureMark Tedesco

Exploring Montichiello: A Hidden Gem in Our Italian Adventure

PART 89: It might be interesting to share how we pulled off living in Italy for part of the year. I will post some steps and what we are learning along the way.

We love every minute of it, and what was once a dream is our life!

We live in Tuscany in the Fall, then back again in the Spring, and in California for the rest of the time (in a previous blog, I explained why we live in Italy only part of the year).

Step 1: As we explore areas and towns in Italy, we discover some gems worth sharing. Some of these are well-known tourist magnets; others are lesser known but always amazing.

This week, let's explore Montichiello.

Step 2: Our experience

Today, we decided to take a break from home renovation (more on that in a future blog) and explore unfamiliar areas of Tuscany. So we hopped in our car, drove towards Pienza, saw a side road with a sign pointing towards the "Medieval Town of Montichiello," and let instinct guide us.

Once we exited our car, we realized we had been there before. Years ago, we visited Tuscany for the first time and saw so many towns and villages that they became a blur. This time, we resolved to give Montichiello the time it deserved.

Walking through the town gates, it felt like we had entered a children's story. The beautiful cobblestone streets were lined with unique stone buildings that housed shops, restaurants, and apartments.

We then walked to one of the main piazzas in town, where a white-bearded elderly man came up to us and welcomed us to his town. He told us he was born there and had lived in Montichiello his entire life. He then asked if I knew who he was.

His question perplexed me, and I wondered if we had met the last time we were there. He repeated his question again: "Don't you know who I am?"

I smiled and said no. "People say I look like Santa Claus, and children constantly ask to pull on my beard to see if it is real." I looked at him in a new light and realized that, yes, he did look like the classic Santa Claus.

At this point, Santa gave us a tour of his beloved town, shared its history, and led us into the main church. Once inside, he explained the meaning of the frescoes, which had been discovered when the church was renovated.

He went on to tell us that the town is known for its summer theatrical productions and that he has been involved as an actor for decades. He asked us to look for the documentary "Spettacolo," which recounts the story of this local theater.

I will share some of this history here.

Step 3: History

Monticchiello, a serene town, has a rich history dating back to Etruscan times. The current fortress, built in the 1200s, served as a defense for the Republic of Siena, making it a valuable asset in conflicts with Montepulciano. Later, the Medicis took control of the area, and in 1777, Monticchiello became a part of the district of Pienza where it remains to this day. Despite its peaceful atmosphere now, the history of Monticchiello tells a different story of conflict and strategic importance.

During World War II in 1944, there was a conflict between the local partisan fighters and the occupying German forces near Monticchiello. In retaliation to the partisan activities, the German army entered the town to slaughter the residents. However, a fortunate incident occurred when a young German woman, who was married to a local man, was present among the villagers. With the help of the village priest, she persuaded the soldiers to spare the people's lives. As a result, all the citizens of Monticchiello were saved from execution.

Step 4: Theater

Monticchiello is a place that attracts many visitors, particularly during the summer when the unique Teatro Povero takes place. The Teatro Povero, or Poor Theater, originated in the 1960s during a period of significant change in the local community. At that time, the traditional agricultural practice of share-chopping was diminishing, people were migrating to urban areas for employment, and significant economic and social changes were happening.

The theater, which involves producing a play based on a theme of local importance, has been a means of community engagement and self-expression for over 50 years. The local theater group chooses the theme, writes, directs, and acts in the play. Every year, a single play is produced and presented as an outdoor event from July to August. In 2017, a documentary film called "Spettacolo" was released, which beautifully and insightfully tells the story of this unique tradition.

Step 5: Cool things

Medieval Entrance

Upon entering Monticchiello, the first eye-catching feature is the well-preserved city walls encircling the town. Dating back to the 1200s, the walls include a grand tower and a gate with a pointed arch, which serves as the primary entrance to the town. Although the gate was initially constructed to protect the town, it now stands as a charming backdrop to the elegant and high-end restaurant Osteria La Porta.

The Pieve dei Santi Leonardo e Cristoforo

The Pieve dei Santi Leonardo e Cristoforo is a magnificent Gothic-style church constructed in the latter part of the 13th century. However, in the late 18th century, it underwent a Baroque renovation that whitewashed and plastered the church's incredible 14th-century frescoes. In the 1930s, an incomplete restoration of the interior began with the aim of uncovering the frescoes and restoring some of the original chapels.

The church's most exciting feature is its colorful frescoes. One touching fresco depicts St Christopher carrying the baby Jesus on his shoulder.

Exploring the streets

In addition to the landmarks, the small streets and medieval homes in Monticchiello are also gorgeous. They are now immaculately kept and decorated with flowers and climbers.

The views

One thing you should not miss when in Monticchiello is the panoramic view just outside the main medieval gate. As you leave the town, the hills of Val d'Orcia roll out before you, offering one of the most quintessentially Tuscan landscapes you could ever wish for! In front of Monticchiello, you can see the hill with Pienza, and from a distance, you can recognize the distinctive shape of Pienza's bastions and duomo.

Step 6: Links

Insights: Getting in the car and exploring by instinct rather than by plan has rewarded us with unexpected discoveries. Today, we burst upon Montichiello and met a resident born in the town who has lived there his whole life. He let us experience "his" Montichiello.

More next time.

Now on sale for $2.99: My book is "Stories from Puglia: Two Californians in Southern Italy." Amazon US:

Amazon Italy- my book "Lei mi ha sedotto. Una storia d'amore con Roma":

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May 05

Looks like this wonderful restaurant, which I ate at 15 years ago, is still open.

Mark Tedesco
Mark Tedesco
May 05
Replying to

Wow! Tell more about it in a comment please! Thanks!

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