The Walled Medievel City of San Gimignano

One of my favorite stays in Italy was at the Guardestelle agriturismo in San Gimignano. It is an adorable working farm, producing wine and olive oil, in the hills of Tuscany. The city of San Gimignano was a short walk away.

San Gimignano is also known as the Town of Fine Towers, and is constructed on the site of a 3rd century BC village. Fourteen of the original towers still exist and it gives the city a beautiful and impressive skyline.

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The San Gimignano skyline.

You feel regal and important as soon as you begin to see the main entrance to San Gimignano. The large stone wall and oversized doorway transport you back hundreds of years and you feel like you should be on horseback, with a knight riding beside you.


The city entrance.

If you’re not impressed enough by the wall itself, just turn around and marvel at the view.


The view is said to inspire popes and poets. I know it inspired me.

As you enter the city you expect to see fair maidens and jesters and everything that you would see at a Renaissance festival. It’s quite spectacular.

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No, I don’t have a time machine, it really looks like this!

We wandered around in the drizzling rain, and the beauty of the countryside in such poor weather is proof of just how amazing it is there.


A little rain won’t stop me!

The town is full of quaint little art shops, wine stores, restaurants, and award winning gelato. You really can’t go wrong here.


I may hang this on my wall.

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Gelateria di Piazza, some of the best gelato our whole trip!

I wish I could have stayed here and lived happily ever after.

One thought on “The Walled Medievel City of San Gimignano”

  1. thought it was just a historic site! I didn’t realise that’s where those cute shops were. Do people actually live there? That’s it, I’m moving.
    Love the picture of you with the umbrella. The umbrella looks right at home

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