7 Reasons Why You Can’t Miss San Gimignano

It’s no secret that Tuscany is one of the most wanderlust-inducing regions in the world. From its wine to its gelato to it’s beautiful medieval architecture, Tuscany has everything you want for the perfect trip.

san gimignano

On my recent trip to Italy, I was fortunate enough to find myself in Tuscany for a few days. While most of this time was spent around Florence, we were also able to make our way to a little town called San Gimignano.

This quaint little area is just an hour away from Florence, and known colloquially as the Medieval Manhattan. It is not only a wonderful Tuscan town, but my absolute favorite place I went to in Italy (and that includes Venice!)

san gimignano entry

Here are the 7 reasons why you shouldn’t miss San Gimignano:

1. It’s the perfect example of a medieval Tuscan town

When you think of Tuscany, what do you imagine? Is it old architecture, cobblestone streets, vineyards? Well, San Gimignano has all of that and then some! When you enter the city, you feel like you’ve truly gone back in time!

san gimignano

2. Amazing Tuscan views

San Gimignano is placed at the top of a hill, which means you can find fantastic views of the countryside from almost anywhere.

At Rocca of Montestaffoli, a courtyard full of silvery olive trees, you can climb a staircase to find a view that will take your breath away.

san gimignano tuscan panorama

3. Best gelato in the world

Florence may be the home of gelato, but San Gimignano is home to an international gelato winner! Gelateria Dondoli has won the Gelato World Championship twice, and you can tell everyone loves it based on the lines.

While the queue can be daunting, don’t fret—it’ll probably take you no more than 15 minutes to get yourself a cone!

gelateria dondoli

gelateria dondoli cone

4. The towers are impressive

Known as the “Medieval Manhattan,” San Gimignano has tons of towers that make up much of the skyline. Today, only fourteen remain, but all are in fantastic condition.

These towers were once built as status symbols, in a small town where palaces just couldn’t fit!

san gimignano towers

5. A cool mix of medieval and modern

Like many areas of Tuscany, this isn’t just some preserved tableau of the past—it’s still a bustling community that people live and work in.

Modern shops line the streets, perfectly integrated into the old architecture. Instead of tearing down the history, the city adjusted and adapted to its existing infrastructure, which is remarkable to see.

Bonus: check out the Medieval Criminal and Torture Museum if you get the chance!

museum of toruture san gimignano

6. Beautiful sunflowers and vineyards

Sunflowers are often used in the imagery of San Gimignano, as they bloom all around the drive up the hill. It really doesn’t get more picturesque than that!

Unfortunately, I went during a time when they were no longer in bloom, but I still passed by countless grapevines of the surrounding vineyards.

san gimignano piazza

7. It’s stunning

More than anything, San Gimignano is just gorgeous. I was enamored from the moment I entered its walls, from its rolling hills, to the views, to the vines that climbed up the buildings. I loved it so much, that I considered giving up Target to live there.

san gimignano

I could have easily spent a few days here, walking around the town and relaxing with some gelato. Alas, I was only in San Gimignano for a few hours, but it was enough for me to implore that it’s a must-see for anyone heading to Tuscany!

What’s your favorite off-the-beaten-path destination? Let me know in the comments!
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2 thoughts on “7 Reasons Why You Can’t Miss San Gimignano

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