• Jay Hicks

The Walled Cities of Tuscany!

Updated: Jun 30


Piazza della Cisterna San Gimignano, Italy

If you find yourself in a few extra days in Florence and you have time to visit the Tuscan country side, make sure you visit some of the medieval cities. Along with fine vineyards, wine and food, you will find numerous walled cities perched on top of hills. Some can not get enough of the Tuscan countryside and eventually make their home. But for the tourist, it is a bit daunting and the best you can do is enjoy, relax, and try not to lament about not being able to see it all.

Eating Pasticcini with Friends in San Gimignano

Drinking cappuccino while eating cornetto or "little horn", in one of the many lovely outdoor cafés in the sun dappled streets of San Gimignano, it would take some time before I realized how fortunate we were. Known as the City of Towers, is arguably one of the best preserved medieval cities in all of Tuscany. With more than seven towers, (Torre and Campanelli), this walled city is a must for anyone interested in medieval times and the renaissance period.

Walls of San Gimignano

San Gimignano, was well-known to pilgrims heading south from Florence to the Vatican. There is no wonder why travelers stopped her on the way to Rome as the stonewalls, old city, cobbled Roads, and blue skies make this place phenomenally picturesque. Long before you arrive in San Gimignano, you can see this picturesque hilltop from the twisting and turning Tuscan roads.


La Buca di Montauto with Boar Salumi Offerings

Known for its ts wild boar sausages, this is a must see for travelers in the area. It turns out that boar has been one of the traditional foods of San Gimignano for hundreds of years. You will find Premium wild boar Taxidermy throughout the city, giving way to the San Gimignano's other nickname of City of the Boar.


Aerial Photo of Monteriggioni - castellitoscani.com

As we headed south on our way to Siena, we pass by the fantastic walled city of Monteriggioni. This location is right along the Florence-Siena highway. Should you find yourself in a pinch for time and can’t make it out into the Tuscan countryside to visit one of the other wall cities, this is a must stop when traveling between Florence and Rome.


You enter into Monteriggioni's, via the Porta Franca gate, where you can find a military museum of ancient weapons, and the 13th-century Church of Santa Maria. Similar in age to San Gimignano, the city is not as large and does not have as many offerings. But, on the highway, with easy access parking, Monteriggioni's is a fantastic place for a quick stop over to see an ancient walled city. In the 1200's it was built by Siena as a front fortress for wars against Florence.

Palio di Siena at Piazza del Campo - Courtesy US News

Siena is a fantastic old walled city, with a lovely AirBnB's and romantic old hotels. There is even a Sheraton for die hard Marriott fans. As always good food abounds, but make sure you take in the cathedral or Duomo di Siena, and the Tower of Mangia. Directly in front to the Tower of Mangia is the fan shaped town square Piazza del Campo, which has many outdoor food and drink offerings and unique shops. In July, be advised the Piazza becomes the venue for one of the top horse races in the region. Siena dates to the time of the Etruscans (c. 900–400 BC) and has the oldest continuing operating bank (Monte dei Paschi) in the world, dating 1472.


Should you find yourself under the Tuscan Sun, visiting one of the walled cities should be on your top list of things to do. If you can, stay the night and the town will be yours after the tourist leave.


Porta Romana of Siena Dating back to the 1400's


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