For those of you who follow me regularly, you know that I have fallen in love with Tuscany. I never tire of talking about it and am pretty sure that at some point in my life, when I decide that I want to slow down a little, I’ll have a second home there. Enjoy Four Must-See Medieval Villages In Tuscany.

Tuscany is, far and away, my favorite destination in Europe so far. One of my favorite things to do is spend my Sundays exploring a new medieval village.

Here are four of my favorite villages in Tuscany.


Four Must See Medieval Villages In Tuscany

San Gimignano 


This 13th-century medieval town is one of the most visited in Tuscany. With that said, its old world feel has not been squeezed out of it to accommodate tourists.

This UNESCO site is surrounded by high brick walls protecting her secrets of times gone by. The wheat fields and vineyards that surround the area add to its untouched and preserved beauty.


Four Must See Medieval Villages In Tuscany


The town was once home to 72 towers and was a resting stop for Catholic pilgrims journeying to Rome during the Renaissance. Over the years, through wars, plagues and economic woes Italy has managed to preserve 15 towers which are a must see when visiting the town. 

Within her walls are magnificent architectural and artistic museums. Two beautifully constructed cathedrals, Collegiate Church of San Gimignano and Chiesa Madonna dei Lumi are breathtaking and worth visiting regardless of your religious affiliation. 

There are many museums to visit and a couple of my favorites are the Medieval Criminal and Torture Museum (yes a bit morbid but still very interesting!) and San Gimignano 1300 which is a unique journey through time. 

San Gimignano is famous for its wine and has wonderful vineyards surrounding the town. Two definitely worth a visit is the Tenuta Torciano Winery and Panizzi. Both offer wine tasting tours with meals. If you’re a wine lover, like I am a visit is a must!


Four Must See Medieval Villages In Tuscany



Driving up to this amazing town perched high on a volcanic rock I immediately fell in love. Surrounded by two rivers, Lente and Meleta, Pitigliano is relatively small but the cobblestone streets and old world feel still holds the spirit of ancient lives that lived and worked within her walls. 

From the outside, the lush green and rocky exterior look completely unchanged and untouched. Scattered on the mountainside are deep caves and tunnels that were used by townspeople and guards to secretly come in and out without notice.

A very important part of Etruscans‘ history the town was once dominated by a powerful family, Longobard of the Aldobrandeschi. Interestingly, Pitigliano is most famous for its influx of large Jewish communities because of the persecution of the Hebrews in Rome. With more than 10% of the inhabitants being of Jewish nationality the city was once known as “Little Jerusalem”.

What you have to do

Located within the city walls are some amazing sites that you must see when visiting this part of Tuscany. Here are a few I highly recommends.

The Orsini Palace. The immense carvings and ornate art is fascinating and shouldn’t be missed. It’s located at the entrance of the town and next to a fascinating medieval aqueduct. 

 The Cathedral of Saints Peter and Paul A gorgeous church is worth seeing. The architecture and art that cover the interior are like none other. Make sure to look up! The paintings are breathtaking.

EAT – It’s Italy of course so what’s a visit to a medieval village without indulging in the local food. It’s rare that you’ll find a bad restaurant and within these ancient walls, you’ll find several, all worth taking your time to work on the menu. My favorites are Hostaria del Ceccottino and Trattoria Il Grillo. The food is exquisite, the service is unparalleled and expect to leave with new found friends. 


Four Must See Medieval Villages In Tuscany



Located between the cities of Montepulciano and Montalcino is the beautiful little commune of Pienza. Also a UNESCO site, it is known as the birthplace of Pope Pius II

Its main square constructed of red bricks is surrounded by buildings that were designed by the architect Bernardo Rossellino commissioned by the Pope to give a powerful and royalistic feel. 

What you have to do while there

The small town is romantic and a throwback to times gone by. It’s easily navigatable and I’d recommend not planning a formal tour. Wandering at your leisure will bring you to points of interest and restaurants that you should try. A half a day is all you’ll need to explore this beautifully designed town.


Four Must See Medieval Villages In Tuscany


On the west side of the village, you’ll find Palazzo Piccolomini. It’s three floors house articulated architecture with interestingly placed windows.

The center square is dominated by the Cathedral and can’t be missed as it is one of the most spectacular architecture you’ll find.

Several places to eat and enjoy a local glass of wine can be found literally every few steps and each one is worth stopping at least to have a look at. 

Easy to pass up, Pienza is a village you should take the time to visit on your way to Siena or other larger points of interest in Tuscany.


Four Must See Medieval Villages In Tuscany



This is my favorite of all the towns that I’ve visited in Tuscany, hands down! After seeing it featured in “Under The Tuscan Sun” and after my, way too close to home, experience, I decided that I wanted to visit Tuscany and particularly Cortona.

There is nothing I don’t love about this charming, ancient town. I visited for my birthday during the summer, a perfect time of year to experience all that this part of Tuscany has to offer.

The town is surrounded by olive orchards, wheat fields, and vineyards. The air is bursting with the fragrances that permeate every corner of the city. 


Four Must See Medieval Villages In Tuscany


Cobblestones cover the streets and piazzas and the cool stone walls hold secrets that no one will ever know. I found myself often reaching out in the hopes that I might feel a little of what life might have been like all those years ago.

Shopkeepers and cafes open early to welcome tourists and locals alike and are always eager to help, whether they understand your language or not.

What you must see while in Cortona


Four Must See Medieval Villages In Tuscany


Of course, you have to visit the Piazza Della Republica. Its 13th-century clock tower was made famous in the movie and it is a beautiful place to sit and have an espresso, lunch, or people watch. (Don’t be disappointed that the fountain in the movie isn’t really there, it was flown in specifically.)

There are several churches that are a must see. The Duomo is built on an Etruscan temple site and is Cortona’s main Renaissance cathedral. Although it has 16th and 17th-century paintings on the inside, the outside is from the 11th century.

Near the public gardens of Cortona is the church of San Domenico which is home to a very well preserved 15th century alter and art by Fra Angelico and Signorelli.

Built in 1245, the Church of San Francesco houses a painting by Pietro da Cortona and the remains of Signorelli himself!

If museums are what you like, Cortona has no shortage of them. My favorites are Museo dell’ Accademia Etrusca which holds remains from Rome, Baroque and Renaissance paintings, and a small Egyptian exhibit.

You can find an actual Roman sarcophagus in the Museo Diocesano. Although small it’s worth a visit to see the fantastic artwork.


Four Must See Medieval Villages In Tuscany


Cortona and the surrounding area is famous for wines. Some of the world’s award winners are grown in the vineyards that call this part of Tuscany home and my all time favorite is produced at Avignonesi Vineyard.

For my birthday I was sponsored on their Tour and Wine Pairing Gourmet Lunch. It was 3 hours of pure food and wine heaven unmatched by any other I’ve experienced. I can’t recommend this tour enough for people who love Italian food and wine.

As with any town in Tuscany, there is no shortage of restaurants that serve a variety of Italian food from all over. You can find small eateries scattered within the town walls as well as pastry and coffee shops. A couple of my favorites are Osteria del Teatro and Ristorante la Bucaccia da Romano both serve amazing delicacies and local wines.

Staying in Cortona is easy. There are many small hotels in the town itself and beautiful resort villas surrounding the area. If you want the full experience I would stay at one of the resorts so you can wake up to the beautiful countryside.

How to get around Tuscany

Public transportation is plentiful and easy in Tuscany. However, many of the places that I have mentioned don’t have easy access to it. Renting a car is straightforward and recommended. You can also join various tours that can be booked through the hotel you’re staying in or via a travel agent.

There are also many private tour companies that you can hire or, like I do, hire a local driver to take you on a private tour of places, off the beaten track and tourist attractions, that you want to see at your leisure. (This is my preferred way to see any country particularly in Tuscany as many of the drivers are easy on the eyes and ears (mine included!)! wink wink

I hope you enjoyed Four Must-See Medieval Villages In Tuscany. They are my favorite and I would recommend them to anyone who wants to see the real Tuscany.

Have you been to Italy? Have you visited Tuscany? Have you spent time in any of the villages in this post? Share your experiences with us!

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