A visit to a walled Tuscan city is a must, but which ones should be on your itinerary? San Gimignano or Volterra? Cortona or Lucca? They each offer something different, so to help you make your choice, here’s a list of the most scenic walled towns and cities in the region, to satisfy your taste for the historic and picturesque.

San Gimignano – The “Manhattan of the Middle Ages”

Half way between Florence and Siena, San Gimignano has to be at the top of the list. It’s a world famous UNESCO site, with a historic centre that maintains a truly Medieval feel. This is thanks to the perfectly preserved Tower Houses that you can see rising up above the city walls – a unique sight even by Tuscan standards. These 14 towers have given it the nickname “Manhattan of the Middle Ages”. Part of the 13th century walls are still intact and so are the Medieval city gates. You can walk along part of the wall and get great views over the city and the surrounding countryside.

Read more about world-famous San Gimignano.

HIGHLIGHTS: Cathedral (Collegiata of Santa Maria Assunta), Civic Museum, Museum of Torture, San Gimignano 300.

=> Nearby Certaldo is a small Medieval hilltop town that also deserves a visit.

Full-Day Tour in the heart of Medieval Tuscany: San Gimignano – the “Manhattan of the Middle Ages”, Siena and picturesque Monteriggioni. Including a typical Tuscan lunch and wine tasting at a Chianti Winery. Unmissable, and… Excellent value for money!

walled tuscan city
San Gimignano – photo @680451 on pixabay

Monteriggioni – A walled Tuscan city mentioned by Dante.

The tiny fortified town of Monteriggioni, 20 km. from Siena, is a must-see on the Medieval trail. It was a stop on the Via Francigena in Tuscany and so famous that Dante Alighieri mentioned its walls in the “Divine Comedy”.

The original city walls are still perfectly intact, modified in the XVI century to adapt to the new methods of warfare . You enter the city gates just as people have done throughout the centuries and can still walk on part of the city walls, thanks to some recently added walkways. A visit to the Armoury Museum will complete the Medieval experience.

Find out why Monteriggioni is like no other towns on earth!

HIGHLIGHTS: City’s walls, Church of Santa Maria Assunta, Armoury Museum.

Cortona – Up on a Tuscan hill. Under the Tuscan sun.

The view of Cortona up on a hill is quite an impressive sight. The centre is protected by the city walls that were first built by the Etruscans in the 5th century BC, when Cortona was part of the League of 12 cities. Part of them are still visible today.

You can still walk along a section of the walls, and the view of the valley below is spectacular. Today the walls still guard the charming Medieval historical centre. Once you’re inside you’ll find plenty of beautiful narrow streets and lively squares to explore.

Discover all the highlights of scenic Cortona, the setting for Frances Mayes’ bestselling book Under the Tuscan Sun.

=> 12 Top Hilltop Towns in Tuscany

HIGHLIGHTS: Etruscan Academy Museum, Diocesan Museum, Basilica di Santa Margherita, Le Celle Hermitage.

small towns in tuscany
Cortona – photo @vidalouca1970 pixabay

Volterra – A Medieval town with an Etruscan gateway

Volterra is a town with a Medieval exterior and an Etruscan heart. Back in the 4th century BC, Volterra was a powerful member of the Etruscan League of Twelve Cities. And it’s quite impressive to think that these walls have been standing for so long. In Medieval times the wall was brought inwards to better defend the city’s decreased population. The Porta all’Arco is the only surviving Etruscan gate and is quite a sight with three weathered heads guarding the entrance. Now that you’re in Etruscan mode, a visit to the Etruscan Museum Guarnacci is definitely in order.

Find out what makes Volterra a unique destination in Italy.

HIGHLIGHTS: Etruscan Museum Guarnacci, Priori Palace, Cathedral, remain of the Roman Theatre.

walled tuscan city
Volterra – photo @Skitterphoto on pixabay

Pitigliano – A town built on tufa

Pitigliano is a truly impressive sight, even by Tuscan standards. Seen from down below, the town seems to be an extension of the hill it’s perched on, as if the buildings are growing out of the tufa rock itself. The Etruscan walls are still visible, and this marks the beginning of the Vie Cave, a system of Etruscan roads in the Maremma that you can still walk along today. Inside this walled Tuscan city, there’s an ancient Jewish Quarter called “Little Jerusalem”, a Renaissance aqueduct and Fortress, and plenty of narrow alleys to get lost in.

HIGHLIGHTS: Orsini Palace, Little Jerusalem, Museo Civico Archeologico.

Discover all the best things to do during your Tuscan trip. One hour drive from Pitigliano you find the scenic walled village of Capalbio, a real delight!

maremma driving itinerary
Pitigliano – photo @lovefromtuscany

Anghiari – Setting of a famous battle painted by Da Vinci

This is the most scenic walled Tuscan city in the province of Arezzo. It is gorgeous at night when the walls get illuminated, and during the day its stone streets are lively with shops and restaurants. Anghiari used to be a very important centre in the Middle Ages. It was here that in 1440 the Medici beat Milan in the famous Battle of Anghiari. A victory that was later portrayed by Leonardo Da Vinci for Palazzo Vecchio in Florence, though the painting is now lost. There’s a Museum about this battle and some Medieval buildings and churches to visit too.

HIGHLIGHT: Santo Stefano Church, Saint Augustine Church, Civic Museum (Taglieschi Palace).

If you like the ideas of picturesque small towns, check out our favourite fairy tale villages in Tuscany!

Lucca – Renaissance city walls still perfectly intact

With lovely squares and delightful churches, Lucca is a prime destination for curious travellers. It isn’t a hilltop town, but its city walls are an attraction in themselves. Huge and powerful, they enclose the city centre, protecting it as they have done since the 1500. They are the only Renaissance city walls still intact in the whole of Italy.

walled tuscan city
Lucca – photo @Mikalu86 on pixabay

The walls were never breached and Lucca managed to remain independent from the Medici. The lower, thicker walls were designed to better resist canon-fire (taller thinner walls were easier to knock down). Today the top of the wide walls has become  a park where you can walk or cycle in the shadow of trees, a peaceful haven when one can forget their original purpose.

Check out our insider’s tips for exploring Lucca.

HIGHLIGHTS: Cathedral, San Michele in Foro Church, city walls, Piazza Anfiteatro.

Have you found your perfect walled Tuscan city? Write to us and let us know which is makes the top of your list.

When planning your trip, check out the best small towns to visit in Tuscany that are well worth including in your itinerary.

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