If like us you are fans of the Middle Ages, you’re in the right place! We’ve put together a comprehensive list of Medieval towns in Tuscany that you should definitely have on your checklist.
From the popular towns of Siena, San Gimignano and Cortona, to personal favourites like Massa Marittima and Poppi, these are destinations that will make even the most hardcore history buff rejoice.
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Most Impressive Medieval Towns in Tuscany to Visit
1. SIENA
With the marvellous Piazza del Campo at its heart, Siena is the queen of Tuscany’s Medieval heritage. Located in a beautiful area in central Tuscany, it’s a must-see destination for anyone with a passion for the Middle Ages. Siena saw its maximum splendour in the 12th and 13th century, and has maintained – in its architecture, atmosphere and taste – a very close link to that illustrious past.
The historic horse race ‘Il Palio’, with its complex rituals and rivalries, is only an example of the long-lived traditions that still permeate Siena and its contrade (historic neighbourhood). Where red brick buildings, flags and coat of arms fill every corner with memories of the Middle Ages.
12 TOP THINGS TO DO IN SIENA, Insider’s Guide
DISCOVER THE BEST OF SIENA WITH A LOCAL GUIDE: TOP SIENA WALKING TOURS
Medieval Highlights: Piazza del Campo with the Palazzo Pubblico, Gothic Cathedral, San Domenico Church with the relics of Saint Catherine, Santa Maria della Scala Museum.
* Once you’ve enjoyed Siena’s historic centre, you can explore 5 Medieval Wonders to See near Siena!
2. SAN GIMIGNANO
Half an hour from Siena you find San Gimignano, known as the ‘Manhattan of the Middle Ages’ for its beautifully preserved tower houses, is the most popular Medieval small town in Tuscany. A real paradise for fans of everything Medieval.
San Gimignano went through an accurate and faithful restoration work in the 19th century, that maintained and enhanced the Medieval look. Walking around San Gimignano today is a bit like stepping into a film set, and despite being very touristy the town keeps its magical atmospheric, with the cobbled streets, the ancient well in Piazza della Cisterna, and the mighty towers.
* Our Favourite Things to Do in San Gimignano
Highlights: Tower houses (you can climb the Torre Grossa), Museo Civico, Cathedral with its 13th century frescoes, San Gimignano 300 and the Torture Museum.
3. MONTERIGGIONI
Surrounded by its ancient walls, the village of Monteriggioni looks like a perfect crown on top of its roundish hill. The silhouette hasn’t changed much in centuries, since the time when Dante mentioned it in his ‘Inferno’, comparing its walls to ‘terrifying giants’.
Once a defensive bastion of Siena for its wars against Florence, today Monteriggioni is proud of its Medieval heritage and keeps it alive in different ways. There’s a small Armoury Museum, where you can try on a (very heavy) helmet, or join the Medieval fans during the Medieval Festival which is held every beginning of July.
4. PISA, The SQUARE OF MIRACLES
At the time when its Cathedral complex was built, Pisa was one of the Maritime Republics, playing havoc in the Mediterranean against the Saracens. In this stunning square (known as the Square of Miracles), every stone speaks of the glorious past of a port city that had its maximum splendour in the 11th-12th century, when it was a commercial powerhouse.
Visiting the stunning edifices in the Square of Miracles – Cathedral, Baptistry, Leaning Tower – you’ll see all the different artistic influences of this once cosmopolitan city: Eastern taste, Gothic flair, Romanesque rigour in Tuscan marble. Join a Cathedral Complex Guided Tour with a Local Guide to learn about the history of the city, and better enjoy this magnificent square. A real feast for the eyes!
IINSIDER’S TIP – f you love Medieval art as much as we do, you should visit the splendid Basilica di San Pietro a Grado Church with its intriguing 13th century frescoes.
5. CERTALDO ALTO
A small Medieval gem, the hilltop town of Certaldo Alto went through a faithful restoration work in the 1800s that perfected the Medieval look. Today this small town near Florence (30 kms.) is a welcoming and lovely destination, with its link to 14th century writer Giovanni Boccaccio, tower houses, a wonderfully restored Palazzo Pretorio and plenty of Gothic charm.
6. POPPI and its CASTLE
Poppi is probably the least famous of all the sights listed in this post. Located in the scenic Casentino Valley, in Eastern Tuscany, this small hilltop town has a flagship, a beautifully preserved Medieval castle that guards over the town and the whole valley. The imposing Poppi Castle, built by the Counts of Guidi who ruled the area since the 12th century, it’s one of Tuscany’s most impressive castles and a personal favourite!
* Check out our Driving Itinerary in the Scenic Casentino Valley
7. CORTONA
Ancient city walls, narrow cobbled streets, a beautiful main square and a bunch of Medieval houses make Cortona one of the favourite Medieval towns in Tuscany. The heart of town is Piazza della Repubblica, a handsome space dominated by the Palazzo Comunale and its staircase. It’s the liveliest spot in town, with tourists and locals enjoying the outdoor cafés. Magnificent views, a couple of museums and beautiful surroundings make Cortona, the town “Under the Tuscan Sun”, a popular destination all year round.
* Don’t miss to visit the suggestive Le Celle Franciscan Hermitage near Cortona!
8. MASSA MARITTIMA
The first time I visited Massa Marittima I found its resemblance to San Gimignano striking. It’s located very near the coast, in Southern Tuscany, and it’s a great place to visit if you’re spending time at the beach, as in the Summer it comes alive with festivals and open air music – it’s one the many music festivals in Tuscany set in scenic location!
If you spend a day in Massa Marittima, you won’t run out of things to see and do. The main square is home to a magnificent Romanesque-Gothic Cathedral (that deserves a proper visit) and some tower houses, plus a couple of small well put together museums and lovely shops to explore.
9. VOLTERRA
Volterra is a popular Medieval town in Tuscany with a long history that dates back to Etruscan times. Perfect day trip for anyone with a passion for history. We love its lively and welcoming historic centre, the scenic main square Piazza dei Priori, the artisan shops where local stone alabaster is turned into beautiful objects of all shapes and forms. You climb to the top of the tower of Palazzo dei Priori for a birds-eye view of the surrounding countryside.
Highlights: Palazzo dei Priori, Etruscan Museum Guernacci, Roman Theatre, Etruscan Gate
10. ANGHIARI
Situated 30 km. from Arezzo, Anghiari is one of the most scenic walled towns in Tuscany. The so-called ‘Borghetto’ , the oldest part of the historic centre, testifies to the strategic role this town had throughout the Middle Ages.
In Anghiari you’ll find an imposing ancient tower, the Badia church founded in the 11th century, and a few interesting museums that explore the history of the town, plus some cool artisan shops.
When to Visit the Most Popular Medieval Towns in Tuscany
We hope you’ve enjoyed our list of our favourite Medieval towns in Tuscany! These are precious places filled with atmosphere and magical things, memories of a glorious past that is still cherished and celebrated today.
We recommend to visit the most popular places – like Siena, Pisa, Cortona and San Gimignano – out of the main tourist season, which goes from June to September. If you come in early Spring, late Autumn of Winter, you’ll be able to appreciate these towns in relative tranquillity, without the crowds!
READ ALSO:
* 10 Non- Touristy Things to Do in Florence
* Looking for the Most Picturesque Villages in Tuscany
* Top Summer Medieval Festivals in Tuscany
Author: Sabrina Nesi, born in Florence, founder of Lovefromtuscany.com, passionate about sharing the beauty of Tuscany and Italy with the world.
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