Medieval hilltop towns are a regular feature of the landscape in Tuscany. Some say its most defining one. With their fortified walls, towers and stone streets, these towns are so well preserved that they give visitors the impression they’re travelling back in time.

None more so than in San Gimignano, Certaldo and Monteriggioni. Here you are in for a full immersion in the Medieval world.

San Gimignano, one of Tuscany’s greatest Medieval hilltop towns

Even by Tuscan standards, San Gimignano has a definite ‘wow’ factor. This well preserved town centre has fourteen towers that stand vigilant over the town. They tell the story of a violent and dangerous era when the most powerful families competed with each other to build the tallest one, both for protection and for show. Here, stone streets and atmospheric squares envelop the visitor inside a world of pure Medieval nostalgia.

History is everywhere here. Enter the Cathedral for its vivid Medieval frescoes. Visit the Torture Museum for a Gothic scare, or sit in the square and enjoy the atmosphere. It is a favourite for tourists, but is no less charming for that. A visit in winter is particularly rewarding when the mist hangs over the city and only adds to the drama.

San Gimignano is roughly an hour’s drive from Florence heading south.

medieval hilltop towns tuscany
San Gimignano – photo @guy-dugas on pixabay

The photogenic red stones of Certaldo

Once you walk through the gate ‘Porta del Sole’, you say goodbye to the 21st century. From the stone arches to the ancient fountain, every thing here demands a photograph. Some of the buildings have been restructured to give them back their Medieval mojo, some crenellation has been added here and there, but doesn’t detract a bit from its authentic Gothic atmosphere.

The small town of Certaldo has developed since the middle ages around the main street Via Boccaccio. At one end of it stands the striking Pretorio Palace. Its facade alone is worth the trip up here. The coats of arms you see here are a common feature in Tuscan Medieval buildings. Their function was to represent the ruling families, but they also add irresistible aesthetic detail to the exterior. The palace can be visited too and so can the House Tower of Boccaccio, from which there is a gorgeous view of the town and the valley below.

Certaldo is 30 kilometres south of Florence, and not far from San Gimignano. To plan a visit, check our post with more useful information about Certaldo.

Certaldo, view from Boccaccio House – photo @lovefromtuscany

The divine walls of Monteriggioni castle

Even Dante, who must have seen his fair share of walled towns in his time, was so impressed by Monteriggioni’s crown of massive walls, that he mentioned it in his Divine Comedy. The town’s position wasn’t casual however. The fortress was built by Siena as a first line of defence in its continuous battles with its rival Florence. After all, Medieval hilltop towns were always designed with security in mind.

The walls are still intact today. You can walk along part of the them and visit the small but entertaining Armoury Museum where you can have a go at swinging a battle sword and wearing a (very heavy) helmet. The atmosphere you’ll find in Monteriggioni, with its narrow stone lanes and picturesque corners, won’t disappoint you. Especially if you have an interest in Medieval history, or you’re a fan of the Assassins Creed games. Speaking of which, in August there’s a Medieval festival and for anyone who likes Medieval reenactments, it’s a must.

Monteriggioni is 12 kilometres north of Siena (40 km. from Florence)

=> Check out the Most Beautiful Castles that you can visit in Tuscany!

Monteriggioni – photo @lovefromtuscany

These three charming towns are among the most scenic walled towns in Tuscany. They are also the guardians of its Medieval past. Atmospheric, soulful and beautifully preserved. Long live the Middle Ages.

For more suggestions about the best destinations to include in your itinerary, have a look at the most scenic small towns in Tuscany.

⇒ Thinking of visiting the hilltop towns of San Gimignano and Volterra? Here’s a brief guide to both towns.

⇒ Discover Massa Marittima, a charming hilltop town in southern Tuscany.