The Tuscan Town They Called the Manhattan of the Middle Ages

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Stand on the road approaching San Gimignano on a clear morning and count what you see. Fourteen stone towers rise from a cluster of medieval rooftops, pointing at the Tuscan sky like fingers from a different century. At the height of its power, this small hill town had 72 of them.

This is why the town earned one of the most striking nicknames in Italy: the Manhattan of the Middle Ages.

The Town on the Ridge

San Gimignano sits on a ridge in the Val d’Elsa, about 50 kilometres south of Florence. It has been a stop on the Via Francigena pilgrim route since the 10th century, and by the 12th century it had grown into a wealthy merchant town.

The wealth came from saffron. San Gimignano’s farmers grew and traded it across Europe, and the money flowed into the hands of a handful of powerful families who now needed somewhere to put it.

They put it in stone — and height.

The Rules of the Race

In medieval Italian cities, towers were more than architecture. They were a statement. The taller your tower, the louder your message: we are powerful, we are wealthy, and we cannot be challenged.

Each family commissioned their tower as a show of dominance. But there was a practical element too. In an era of constant violent feuding between rival factions — the Guelphs who supported the Pope, and the Ghibellines who backed the Holy Roman Emperor — a tower gave you a military advantage. From the upper floors, you could rain arrows on enemies in the streets below.

So families built upwards. Then built higher still. Towers grew not because anyone needed more rooms, but because no one wanted to be second.

At its peak, San Gimignano had 72 towers. For a town of a few thousand people, that was a staggering skyline — more vertical stone per citizen than most modern cities.

What Life in the Towers Was Like

The towers were not comfortable. Rooms were narrow and dark. Stairways were steep and unlit. Some towers reached 50 metres but were only a few metres across at each floor.

According to local accounts, some families built wooden bridges between their towers, creating elevated walkways so they could move between buildings without descending to the dangerous streets below. The ground was not safe territory in a feuding town.

Life was conducted at height, or not at all.

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The Plague That Stopped the Race

In 1348, the Black Death arrived in Tuscany. San Gimignano lost more than half its population in months. The families who had driven the tower race were decimated. The wealth that had funded it evaporated.

The town never fully recovered. It shrank, lost its civic autonomy to Florence, and stopped growing. And this is exactly why it survived.

Because San Gimignano never expanded into a major city — never tore down its medieval centre to build Renaissance palaces or Baroque churches — the bones of the 13th century remained. The 14 surviving towers are among the best-preserved medieval civic towers in Europe. They exist because of catastrophe, not careful preservation.

The Torre Grossa and Civic Pride

Not all the towers belonged to families. The tallest surviving one — the Torre Grossa, or Big Tower — was built by the town itself.

The commune commissioned it in the 13th century specifically to assert authority over the private families who were outbuilding each other. At 54 metres, it declared that no family tower would ever be permitted to surpass the civic one. Even local government couldn’t resist joining the race.

Those same medieval craftsmen whose legacy still shapes Florentine traditions today would have recognised the impulse — in Tuscany, pride in craft and place has always run deep.

What to Expect When You Visit

San Gimignano is a UNESCO World Heritage Site and draws large crowds in summer. Arrive early — before the tour coaches fill the narrow lanes — and you will have the piazzas largely to yourself.

The Piazza della Cisterna is a beautiful irregular square ringed with medieval palaces. The well at its centre has been there since the 13th century. The climb up Torre Grossa takes about ten minutes, and the view across the Val d’Elsa to the wider Tuscan landscape is one of the finest in the region.

The town is also known for its Vernaccia di San Gimignano — a crisp white wine with DOCG status that has been produced here since the Middle Ages. The towers were built on saffron money. The wine is what stays with most visitors now.

The families who built those towers are long forgotten. Their names, their feuds, their obsessive need to be tallest — all gone. But the towers remain, casting the same long shadows they did 800 years ago, still the first thing you see as you approach along the Tuscan road.

Whatever they were trying to prove, they proved it. Just not in the way they intended.

You Might Also Enjoy

• The Ultimate Tuscany Road Trip Guide — plan a journey through vineyards, hilltop towns, and medieval villages
• The Florentine Leatherworkers Who Refused to Let a 700-Year Craft Die — another story of medieval tradition that survived against all odds
• Why Italians Feel More Loyalty to Their Town Than to Italy Itself — the spirit of campanilismo that explains why the tower race made perfect sense

Plan Your Italy Trip

Ready to see San Gimignano for yourself? The Ultimate Italy Travel Guide has everything you need to plan your trip — from when to go and where to stay, to the experiences most visitors miss.

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