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Tuscany's Must See Hill Towns

Updated: Apr 27, 2023

In our upcoming episode of Florence & Me, Giulia and I will be discussing how important it is too visit as many places as you can before moving to Italy.

These hill towns have their own personality and charm. I recommend visiting these for an authentic Italian experience.

San Gimignano has a historic city center, preserved through time. It has 14 remaining 13th century towers that showed wealth and protection back in the Middle ages. There’s one that you can climb called Torre Grossa, where you can see a gorgeous panorama of Tuscany.

Cortona is most famous for the movie Under the Tuscan Sun, however there’s much more to this very high hill town. There are plenty of shops and restaurants you can enjoy. I loved wandering the many side streets for great photo ops.

Volterra is much less touristy than the previous two, which makes it easier to explore without huge crowds. The main piazza houses the oldest town hall in Tuscany, Palazzo dei Priori. There are charming museums and many alabaster workshops to visit. The countryside surrounding it is breathtaking as well. A little known fact, Volterra was the lookout point for the

Pitigliano is one of the most impressive hill towns. It’s located in Maremma carved from volcanic stone. Le vie cave known as “excavated roads” are still confusing for historians and archaeologists. They were of great importance because they required the removal of 40,000 tons of volcanic rock. One theory is they were used for water flow, another is they were created for sacred Etruscan rituals. Either way, you can visit them on your own or with a guide. This is on my list to visit.

Monteriggioni is a Medieval hill town that has been preserved with walls on a low round hill. This was built by the town of Siena as a defensive fort against Florence. You can walk along the walls and visit the Armoury Museum.

Certaldo Alto is a quaint small hill town about 30 minutes from Florence. It has only two streets but there’s still enough to do and see. This includes the house of Medieval poet Boccaccio who wrote the Decameron and Palazzo Pretorio. There’s a few shops and family restaurants to taste the town's delicacies.


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