Monteriggioni – Another Hilltop Town in Tuscany

Monteriggioni Photo by Margie MiklasSeveral 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 Photo by 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.

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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.

 Monteriggioni Photo by Margie MiklasPiazza 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.

Monteriggioni Photo by Margie MiklasOther 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.

Monteriggioni Photo by Margie MiklasEverything here is very old and I had the sense that time had stood still.

 Monteriggioni Photo by Margie MiklasEvery 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

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42 Responses

  1. Frank

    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.

  2. karenincalabria

    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!

    • margieinitaly

      Thanks are right…It isn’t at all is very small…you can see it all in a few hours, or of course linger there a ittle longer to fully enjoy it

  3. jimtrish

    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. 😉

  4. Jack Erickson

    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.

    • margieinitaly

      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

  5. enirofral

    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.

    • margieinitaly

      Grazie enirofal-
      Your trip sounds great, and I have found that by asking sometimes your host is happy to oblige..Buon viaggio!

    • margieinitaly

      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.

  6. Stacy di Anna

    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!

    • margieinitaly

      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

  7. Greg Speck

    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.

    • margieinitaly

      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

  8. stellalucentellc

    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…

  9. philipstrange

    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.

    • margieinitaly

      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

  10. imarancher

    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!

  11. Tony

    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! 🙂

  12. bonniegm

    Love Monteriggioni – stop by every year. Piccolo Castello is a wonderful restaurant with garden dining.

I'm always interested in your thoughts, so please leave a comment.