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Castiglion Fiorentino, cozy fortified village with a view of the Val di Chiana in Tuscany

Castiglion Fiorentino in the Tuscan Val di Chiana is a charming and cozy fortified village with good connections
Castiglion Fiorentino in the Tuscan Val di Chiana is a charming and cozy fortified village with good connections (photo: Edward Hendriks, other photos: Sarah Monni)

As the child of an Italian father, I have traveled quite a bit to the country I call my second home. I could already tick off Sardinia, my father's birthplace, the largest cities in Italy and the Amalfi Coast. But Tuscany – which in my opinion is the epitome of what many people imagine Italy to be – was a place that was still high on my list. Last summer I was finally able to see the world-famous region with its rolling hills in real life. From the village of Castiglion Fiorentino to be precise.

I actually ended up in this village by chance, because I and my boyfriend were looking for a quiet place with good connections to nearby cities. It certainly was that, and more.

By train through the hills

To reach our destination, we first took the plane from Amsterdam to Florence. From Firenze Santa Maria Novella station we could then take a direct train to Castiglion Fiorentino.

After arriving at the picturesque train station, I immediately got into the holiday mood. We continued to our home on foot B&B: Il Melograno. A completely private holiday home with its own swimming pool, surrounded by a large garden. Of melograni, pomegranate trees, of course. The perfect base for a relaxing holiday in a typical Tuscan village.

Painting at the front door of 'Il Melograno'

Medieval village with Etruscan influences

At first glance, Castiglion Fiorentino looks very medieval. Located on a hilltop, surrounded by thick stone walls. However, there are also influences from the Etruscans, who founded a settlement in the area. You will also spot a lot of architecture that clearly dates from the Renaissance.

Another fun fact: Roberto Benigni, one of Italy's most famous actors (including from La Vita è Bella) comes from this versatile village. Doesn't have much to do with history, but I couldn't resist mentioning it.

The municipality of Castiglion Fiorentino will be happy with the honorable mention, because they are clearly proud of Benigni. There is a statue of the actor in Manciano-La Misericordia, a hamlet within the municipality.

The view from the B&B

Scenic views

If you come to Tuscany for picture-perfect pictures of the well-known hilly landscape, you are in the right place in Castiglion Fiorentino. The plains of the Val di Chiana are exactly as you expect from Tuscany. Extensive green hills with the characteristic long cypresses in between.

From several places in the village you can enjoy views that seem straight out of a painting. One of these places is the Loggia on the Piazza del Municipio. The Loggia was designed by the famous Italian painter and architect Giorgio Vasari. There are two cozy cafes under the imposing arches. Enjoy breathtaking views while drinking a cup of espresso!

Climbing the tower

Another spot perfect for seeing Castiglion Fiorentino from above is the 14th-century Torre del Cassero. The tower was once part of the medieval fortress from which the village was protected. Nowadays, the walls of the fortress are no longer completely intact, but it is still possible to climb the tower.

Torre del Cassero Castiglion Fiorentino
The Torre del Cassero in the middle of the historic center of Castiglion Fiorentino (photo: Edward Hendriks)

At the time we did this, we were the only tourists in the tower. That was no exception, because it was very quiet during the period that we visited the village. While climbing the tower it was nice that we were alone. The stairs were very narrow and made of creaky wood.

The height of the climb itself was not too bad, the tower is about 35 meters high. In any case, the effort was more than worth it, because the view from here is also fantastic. After visiting the tower we could continue the historical tour, because next to it are the excavations of an Etruscan temple from the 6th century BC.

These sights are both good for the wallet, because they are completely free. Please note that you only have access to the tower on weekends.

Castiglion Fiorentino view of the Val di Chiana
The view from the Torre del Cassero

Pici, pizza and panzanella

In Italy you can eat great food everywhere, no matter which region you are on holiday in. That's a fact. Tuscany is certainly no exception. Although Castiglion Fiorentino is a fairly quiet village, you will find plenty of restaurants, cafes and other eateries. With classic Italian food such as pizzas, but also with Tuscan specialties.

For example, we ate handmade at Il Ristoro di Via Dante pici, a typical Tuscan type of pasta that is reminiscent of slightly thicker spaghetti. If you also want to enjoy beautiful panoramas while eating, then 'GARDEN' is the place to be. This restaurant is located in a green part of the village, just on the edge of the center. The wooden tables with thatched parasols provide a cozy picnic feeling.

The menu is not necessarily quintessentially Italian, but very diverse. You can order a pizza slice or a panzanella salad, but you can also go here for burgers and fried snacks. For the very best pizza you have to be just outside the center, a fifteen-minute walk away. You will find Fratelli d'Impasto in the middle of a residential area. The pizzas are prepared in a Neapolitan way, so there is nothing Tuscan about them. But very tasty.

Pici al cacio e pepe with caramelized onion

Explore the area from Castiglion Fiorentino

As mentioned earlier, I was looking for a location from which it was easy to visit other places. Castiglion Fiorentino is perfect for this. We did everything by train, which was very easy to do.

You'll be there within an hour and fifteen minutes Florence, and within just over an hour and a half you'll be in Perugia. In this area you almost feel stressed about choosing, because there is a lot that is worth visiting. In addition to the cities mentioned, Siena, Montepulciano and Arezzo are easily accessible.

And do you not have a swimming pool at your accommodation, but would you still like to take a refreshing dip? Then you will be on the edge of it in less than half an hour Lake Trasimeno, which is certainly not inferior to a Garda or Como. Unfortunately, I was only able to admire the lake from the train this time, but one thing is certain: I will come back here. 

Castiglion Fiorentino offers plenty of accommodation options

Written by Sarah Monni

Sarah was born and raised in the Netherlands, but Italian culture was introduced to her at an early age. She owes this to her Sardinian father, a man with a great passion for his (island) country. But also to her Dutch mother, who has seamlessly adopted the intricacies of Italian cuisine. In her youth, Sarah mainly visited Sardinia a lot, but nowadays she also travels to other regions of Italy to discover them. As a freelance writer, she would like to share her love for her second homeland with the readers of This Is Italy.

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