Posted by: Debra Kolkka | July 22, 2015

Castiglion Fiorentino

There are thousands of wonderful old villages to visit in Italy. Some are in green valleys, some cling like limpets to hillsides and lots sit prettily on the tops of hills.

We called in to hilltop gem Castiglion Fiorentino  on our way from Arezzo to Cortona. The Etruscans appear to be the earliest inhabitants, and remains of a temple have been found beneath a 12th century church.

We parked just outside the town and walked through Porta Fiorentina in the city walls.


Castiglion Fiorentino

We found a lively main street lined with shops and cafes. It is great to see a thriving community in an old setting.

Castiglion Fiorentino

The town is well cared for and there are pretty narrow streets.

We came upon the Logge del Vasari, which is attributed to Vasari, but was actually built by master craftsmen Bernado del Ghirba and Filippo Bellinzona in 1513. Vasari restored it  between 1560 and 1570 when the Medici coat of arms was added and the walls plastered white with stone mouldings. The colourful chairs were part of an art installation.

Castiglion Fiorentino

There are spectacular views of the Val di Chio from the stone arches.

Castiglion Fiorentino

Castiglion Fiorentino

On the other side of the road is the impressive Comune building which boasts a gorgeous staircase from 1560.

Castiglion Fiorentino

Castiglion Fiorentino

A walk up the steep street beside the building will take you up to the town’s fortress, the Cassero which was completed in 1367. In the 15th century the fortress was occupied by the nuns of San Girolama. By the 19th century much of the fortress had been destroyed and some of the remaining structure was used as a prison.

Castiglion Fiorentino

There were some impressive views from this side of town too.

Castiglion Fiorentino

Torre del Cassero still stands. It was rebuilt around 1350 under Perugian rule. The tower stands on a former base.

Castiglion Fiorentino

Castiglion Fiorentino

Castiglion Fiorentino

There is a lovely park at the entrance to the town, a great place for the locals to gather.

Castiglion Fiorentino

Castiglion Fiorentino is home to many festivals, including the Palio dei Rioni, which is a horse race around Piazza Garribaldi with flag waving and others marvels. It dates back to the 13th century. It is held on the 3rd Sunday of June…we must return.


  1. That tower is quite impressive…and the town…I never get tired of seeing these lovely Italian towns. I like imagining their Medieval backgrounds…you know it was dramatic and bloody, most likely. Lots of intrigue and power play.

    • I am happy to look at these lovely old towns, but I think life must have been very hard back then, especially if you were not rich. Only the tough survived in those days.

  2. I have never seen a tower like that – it is amazing! Thanks for all the lovely photos.

    • There is an endless supply of fabulous old towns to visit. This one was very pleasant.

  3. The view is amazing and the narrow streets, I love them. The tower seems so beautiful, Thank you dear Debra, love, nia

    • Castiglion Fiorentino was a lovely place to stop for a while.

  4. You would be a wonderful tour guide to an endless stream of regional gems.

  5. It is interesting to see how the town changed names throughout history, from the original Castiglione, to Castiglione Aretino, then, Castiglione Perugino, followed by Castiglione Fiorentino, which finally becomes the current Castiglion Fiorentino . It all depended on who was in power…
    Nice photos, Deb!

    • I did wonder about the name and why there is no vowel and the end of the first bit…quite unusual.

  6. Another beautiful place. I find walled towns are always a draw.

  7. Debra, your pictures give me instant wanderlust! The walled towns are something, aren’t they?Love the views from Val di Chio

  8. It always amazes me when I visit Europe and see how old buildings are! 😀

  9. […] visited Poppi, Castiglion Fiorentino , Cortona and Arezzo, a firm favourite. I don’t know why more tourists don’t visit […]

  10. Thank you, Debra, for this lovely overview of our beautiful paese Castiglion Fiorentino. We are saving one of the hidden gems in the town that has been abandoned and boarded up for fifty years. Look for it on your next visit! 🙂

    • The town was a lovely surprise. Well done saving the house. It is excellent to see these houses live again.

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