Next town over…

October 28, 2013 / Places
Castiglion Fiorentino, Tuscany

All too often skipped over for its better known neighbor Cortona, Castiglion Fiorentino is just as lovely, has just as beautiful a view, and is just as deserving of a visit. (And is devoid of the crowds.) As for Tuscan sun, we’re guessing it gets just as much (it’s just 13 kms. or 8 miles up the road, along the same ridge, with the exact same exposure), but it was cloudy when we went so we’re not promising…


Driving up to it you’ll understand why the Perugini, Senesi, Aretini and Fiorentini beat each other senseless over it for centuries. It lords over the entire val di Chiana below, and it’s built like a brick… well, let’s just say that usually any town called “Castle”-something tends to be worthy of the name. Seems those Etruscans again had already fortified their arx/temple up top way back when – (note coming soon.) Then, the town that grew around that nucleus over time was fortified in turn. Could this have made it too worthy a conquest for its own good? Seems it went back and forth between being Castiglion-Aretino, -Perugino and -Fiorentino multiple times. So much for inexpugnable…


The main piazza, like those of so many other similar towns, is a gem. Flanked on three sides by civic and religious buildings, the fourth side is an elegant, nine arch loggia built along / on top of a section of city’s defensive walls. While the back of the portico is mostly walled, three of those back arches open spectacularly onto the countryside (and the drop straight down). Kudos to Vasari, our proto-art-historian, who came up with that colpo maestro (masterstroke).


Head over on the last Sunday of any month and you’ll catch its mercatino. Lots of fun garbage/treasures to be found, like any self-respecting flea market.




by GB Bernardini

Editor, Italian Notebook

14 Responses to “Next town over…”

  1. Michael Murphy

    Delighted to see Castiglion Fiorentino in the notebook. Great photos. Hope you will try again on a sunny day. It really sparkles then.

  2. Anne Robichaud

    Ah, Italy, “land of the endless treasures” – some well-known and others not.
    Been to Castiglione years ago and thanks, GB, for the reminder that it’s time to go back

  3. More delights…and I saw several items I would be tempted to try to stuff into my luggage! Grazie for sharing this little treasure…

  4. R.J. Mardi

    GB, thanks for another great slice of Italy. One more addition for my must see slices of Italy I.N. list. In stead of 2 weeks every other year, when I hit the lottery it will be at least one month EVERY year. Great photos.

  5. GB, It looked familiar, but I’m not sure we visited this town. Maybe it looked familiar because the photos were so convincing and revelatory. Arthur

  6. Alexander A. DiSanti

    What a delightful description for what is clearly a place worth visiting. I have been to Cortona and wish I had known about tis charming neighboring town. The photos were wonderful as well.

  7. While some folks may think all these Tuscan and Umbrian castle hill towns in central Italy look alike, none do and each has someitng different that’s set’s it aside in your memory. Grazie…

  8. Thanks to talk about my beautifull town ! I was born and I leave and work here , I recommand a visit to appreciate the tuscan life stile….. good food …good wine…arts…nature and more other.
    from Castiglion Fiorentino with Love ! Lidia Castellucci

  9. Four years ago, my wife and me stayed in this town for three weeks. Very,very nice town, and people !

  10. Thank you for this lovely piece on our beautiful Castiglioni! We are saving an abandoned baroque chapel in the historic center of the town — in the very area where your photos were taken. You can learn more about our project here:


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