Several years ago I spent ten glorious days in Tuscany, making Siena my hub so that I could take day trips from there easily. On the way home from visiting some wineries, I was fortunate enough to be able to stop in the small hilltop village of Monteriggioni.
This tiny commune in Tuscany is only 15 km from Siena, and is situated near Castellini in Chianti and Poggibonsi. What makes visiting this town so interesting is its fascinating history as an intact walled medieval town which looks much like it did centuries ago.

Photo by MONUDET https://www.flickr.com/photos/monudet/
Monteriggioni is very impressive as you approach on the autostrada and catch a glimpse of it perched high on a hill like a fortress. In the thirteenth century Monteriggioni was built by the Sienna people to serve as a buffer and front line in Siena’s long-standing war with Florence. The strategic location of Monteriggioni made it useful as a fortified defense for Siena. Ultimately however, Siena lost its war with Florence.

Photo by http://www.monteriggioni.info/
I loved walking around this uncrowded town, where only 52 people reside today. Monteriggioni is completely encircled by well-preserved walls which are 10 meters high and measure 570 meters all the way around. Architecture lovers and history buffs find this place particularly intriguing and especially enjoy the fourteen towers which rise above the town from different points in the walls.
The town of Monteriggioni actually was a castle built in 1213 A.D. and the entrances to the town are through two gates. The northern gate faces Florence and is called Porta Fiorentina, and the Porta Romano gate faces south towards Rome. An aerial view of this town looks like an almost perfect circle with miniature houses inside its walls.
Piazza Roma is the main piazza in Monteriggioni and is very large with a simple Romanesque style church of Santa Maria Assunta which dominates the square.
Other small shops, a hotel, a gelateria and restaurants occupy the square, but I wandered past the piazza and found small alleys where the local people live.
Everything here is very old and I had the sense that time had stood still.
Every July during the first and second weekends, Monteriggioni proudly celebrates Festa Medievale, a Medieval Festival. Locals dress in medieval costumes, play music and put on shows using ancient instruments. The piazza suddenly is filled with people from the surrounding communes as well as visitors from other parts of Italy and Europe. It would be a great time to visit for a completely different experience.
Have you been to any hilltop towns in Tuscany? I’m always interested in hearing about your experiences, so please leave a comment.
Grazie and ciao
If you haven’t been to my Instagram page, please check it out…Lots of photos from Italy there.
Love Monteriggioni – stop by every year. Piccolo Castello is a wonderful restaurant with garden dining.
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Thank you Bonnie. Great to know about Piccolo Castello!
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Monteriggioni is lovely and i love that it’s mentioned in Dante’s Inferno!
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Grazie Cristina. I didn’t realize that. Thank you for sharing
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‘Come in su la cerchia tonda,
Monteriggioni di torri si corona’
canto xxxi, lines 41-42
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I did not know that either!
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I also visited Monteriggioni after visiting some wineries in Chianti and loved it! It was great to explore such a quaint, history filled town. Many of the pictures I took look just like the ones you shared in this post. It brings back great memories! 🙂
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Thank you Tony. Glad to hear you visited this medieval town too. Funny how our paths seem to have crossed
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Thanks Tony. I’m surprised how many Italy travelers have been to this charming village
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My favourite is Montemerano..
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Grazie
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It is worth a trip to Italy just to soak in the ambience of this wonderful place. Imagine living there and trusting the walls to preserve you from roving bands out of Florence. Scary times then, hopefully tourists are kinder!
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Thank you Bonnie. Glad you enjoyed it
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A favourite place. I remember eating at ‘Il Pozzo’ – divine. Hope it is still there.
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Thank you Francesca. Great tip!!
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I visited Monteriggioni as part of a walking holiday in Tuscany, it was deep December and I have very good memories of the place and a “very local” bar. The town has an important place in World War 2 history I believe.
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Thank you Philip. It is interesting about World War 2. I will have to review my history. Glad you have such wonderful memories. Thanks so much for stopping by and commenting
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This has been added to my list of places to see! Beautiful photos Margie…
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Grazie Diana
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A great read.
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Thanks for the wonderful photos, Margie! Every time I read your blog I am transported for a bit back to Italy! I will be in Rome in July this year if all goes well, so thank you for the tip about the medieval celebration in July as well. A day trip may be in order…
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Grazie Kathryn! Wonderful I will look forward to your photos this summer
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Brings back memories Margie! The portal at the rear of the town has the most amazing view of the countryside. I love the smaller towns and villages, fewer crowds and a much slower pace.
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Thank you Greg. I remember but unfortunately I don’t have photos from that view as we were pressed for time. I guess it means I’ll have to return
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I too love this little town. It was suggested in a guidebook as a nice place to visit with kids, which we did when my kids were 13, 11 and 4. Even though it was summer, Monteriggioni was quiet, and we could let our kids enjoy the town without having to be such watchdogs (quite a change from Rome and Florence!) And I completely fell in love with the church. I have gone back to Monteriggioni just to be able to say hello to the church. Thanks for bringing back good memories with this post!
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Grazie Stacy -Glad you have been able to experience this amazing place..and I am happy I was able to jog some good memories for you as well. Thanks so much
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another town i wish had a train station
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Thank you Eileen – Sometimes it is worth it to hire a driver to take you to these out-of-the-way gems in Italy but I understand. This place is just to small for a train station.
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On my next trip to Italy I will be staying for 3 days in Colle di Val D’Elsa, which is just besides Monteriggioni. My host has suggested we could visit San Giminiano, but if I can make a special request, I will sure mention Monteriggioni.
I love when you post about tiny villages, thanks for this one.
Line
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Grazie enirofal-
Your trip sounds great, and I have found that by asking sometimes your host is happy to oblige..Buon viaggio!
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Reblogged this on Travel Associate.
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Thanks you for reblogging
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Wonderful photos and commentary Margie. My wife and I spent a night at San Giminiano on our honeymoon in ’01, train from Firenze to Poggibonsi, local bus to San Giminiano. A couple years later we spent a few days at an agriturismo outside Montepulciano.
The Tuscan countryside is spectacular, seemingly little changed from times of medieval pilgrims making their way to Roma.
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Thanks so much Jack..Tuscany has s many small villages to explore. You could spend a year there and never see everything. I appreciate your taking the time to eave a comment
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After your coverage and all of those accolades from the readers, how could you not want to go there? Looks charming and slow. I love it. Next time. 😉
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Grazie!!! I hope you do plan on it….
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Wow! That’s a long, well-preserved wall! Thanks for sharing. I haven’t ever been there. Great recommendation, and it doesn’t look crowded!
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Thanks Karen..you are right…It isn’t at all crowded..it is very small…you can see it all in a few hours, or of course linger there a ittle longer to fully enjoy it
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How wonderful you were able to visit such a marvelous place! Thanks for sharing it and your photos. I’ve been researching a lot about Rome, so it’s nice to see what parts of Italy look like. http://tabathamorrow.com
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Thank you so much Tabatha..I look forward to checking out your site about Rome!!
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Reblogged this on Livedinitaly's Blog and commented:
Taken back in time …
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Small tucked away village visited this pass September by my wife and I. Spent couple hours exploring this medieval fortress outside of Sienna. One of the great things about Italy, never know what’s around the corner. Drove to 31 medieval cities, towns and villages in tucany during September and part of October. Looking forward to returning soon.
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