The Charisma Of Castiglion Fiorentino

unnamed (11)

Magic is alive in Italy and the vast majority of it is found in the medieval walled hilltowns that dot the landscape. The preservation of tradition, the old ways, and the  ancient sites lead directly to the heart and soul of a community. It is here that one begins to truly understand the Italians and their culture.

I arrived in Castiglion Fiorentino on a late Fall day as the sun began to cast shadows over the land. The small Tuscan city looked enchanted, touched by the waning sun’s golden glow. Located between Arezzo and Cortona, it is a small walled city on a hill that is known for its annual festivals and ancient Etruscan sites. Tradition runs deep here and there resides within the locals a fierce loyalty and pride for their community, past and present.

unnamed (7)

After passing the Porta Fiorentina, one of the three old original gates to the walled medieval town, I found Residence Le Santucce, the expansive stone convent which would be my lodging for the next few nights. Seriously impacted by WWII, it rose huge and austere in appearance yet artistically embellished to provide a sense of welcome.

Over the next few days I discovered Castiglion Fiorentino to be every bit as charming as I expected, and more. The entire historical district is easily accessible by foot and well worth the stroll. Here are a few of my favorite things that left me with a good sense of what Castiglion Fiorentino is all about, not to mention the warm and friendly people.

unnamed (13)

First was the Porta Fiorentina, which leads into the historic center of town. Massive wooden doors stand open at the old archway and quickly give one a sense of feeling quite small. Originating from the 13th century, it has stood the test of time and witnessed many human affairs. The colorful Palio dei Rioni, a horse race similar to Siena’s Palio, has been held the 3rd Sunday of June since 1977 near the Porta. Horses race around Piazza Garibaldi, preceded by an extraordinary parade of flag wavers, dames, knights, and musicians.

unnamed (4)

Next is the Cassero Tower, part of the old castle, which stands at the top of the town.  It is a legacy of the Perugian domination in the mid 1300’s. While under their authority, the Casseretto, a small fortress inside the larger Cassero, was built with accompanying high walls that are partially collapsed today. The Caseretto was the last defensive bulwark built. Within was found a well thought to be essential to the survival of the people during a long siege. Large amounts of majolica and glazed pottery remains have been found during excavations which assumes a good number of artisans in the area at the time.

If you love medieval and renaissance art, you will enjoy the art gallery, or pinacoteca, which is very close to the Cassero Tower. It is housed inside the old church of Sant’Angelo and contains religious art collected from the local monasteries and churches. Famous painters with works on display include Taddeo Gaddi and his Maestà from 1328, Bartolomeo della Gatta’s paintings Saint Michael Archangel (1480) and Stigmata of St. Francis (1486). There is also a fine display of medieval jewelry in the sacristy (that I’d love to play with).

unnamed (9)

Castiglion Fiorentino has produced many Etruscan artifacts through excavations that are housed in the Archaeological Civic Museum near the pinacoteca. The museum also has an interesting display of precious ancient and renaissance majolica ceramics as well as relics from the middle ages.


Fronting the Piazza del Commune, the central square, is the nine arch Le Logge Vasariana. It is a renaissance arcade next to the town hall that provides an elegant filter between the Piazza and the lush Val di Chio below. The panoramic views are astounding.

Architect to Grand Duke Cosimo I, Georgio Vasari built the loggia during the early 1500’s when the Medici coat of arms was placed outside the walls. Interesting to note are the pillars and moldings of the stone arches from the white plastered base which displays the Florentine tradition developed by Filippo Brunelleschi, whom Vasari knew well. It is adorned by the coats of arms of the town podestà (mayors) and commissioners.

Some of the arches of the loggia overlooking the valley have been walled in to protect  markets in the piazza from the wind.

unnamed (6)

Below the town and only a few miles away stands the 10th century Castello di Montecchio, perched on a hill. It is stunning to look at and easy to photograph. The turreted walls, the tower, and parts of the mansion can still be seen along with the well-preserved surrounding walls. It is one of the last and most authentic medieval fortresses left in Tuscany. Once given to the British mercenary John Hawkwood, it is now privately owned and used for special events.

unnamed (15)

What about you? Have you had the pleasure of exploring one of Italy’s unforgettable hill towns? What was your impression? I’d love to hear your thoughts so feel free to leave a comment below.

Click here to learn more about Castiglion Fiorentino.




2 thoughts on “The Charisma Of Castiglion Fiorentino

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s