New York of the Middle Ages

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San Gimignano on the Via Francigena

Truly great hiking trails are a mix of four elements, and the Via Francigena – stretching for nearly 2000 km from Canterbury to Rome – has them all.

Firstly and secondly, the Francigena Way features beautiful landscapes and variety: the combination that defines any “good” hiking trail. On top of that, it also offers a historical dimension: as the old pilgrimage trail from northwestern Europe to the “centre of Christianity”, the Via Francigena manages to connect you to history on a personal level, allowing you to follow in the footsteps of all those pilgrims who have come down this way since the Middle Ages.

"Along the Via Francigena"

Unfortunately, however, walking the entire Via Francigena would also take as much time as it did all those hundreds of years ago – i.e. roughly three months. Which is why few people walk all the way and why most hikers concentrate on certain stretches of the trail, mainly those in Italy, or, to be even more specific, on the last 20 or so stages through Tuscany and Lazio.

Read also: The Celestial City of the Via Francigena

Not least because this stretch, more than the others, has the fourth ingredient that makes a trail truly great: which is that special something, the defining element that no other trail can provide. Just as the Saint James’s Way has its unique spiritual dimension and the Rheinsteig has its castles above the river, the southernmost stretch of the Via Francigena is defined by its vistas of Tuscan hilltop towns whose skylines seem to grow out of the green rolling hills like Brigadoon or something from Planet Of The Apes.

"San Gimignano the New York of the Middle Ages"

The most impressive of these hilltop towns is San Gimignano, best approached on foot so you can take it in gradually and understand why some people call it the New York of the Middle Ages.

"Towers of San Gimignano, the New York of the Middle Ages"

Beyond the superficial similarities: after all, San Gimignano even has its “twin towers” …

"Twin Towers of San Gimignano the New York of the Middle Ages"

… there are some deeper affinities, too.

The vertical growth of either city was not driven by any need of large institutions (church or government) to represent and to display strength, but merely by commerce, or, more to the point, commercial rivalries: most of the towers in San Gimignano were vanity projects of patrician families who had earned their money from the trade in agricultural goods, chiefly saffron and wine.

Read also: In the Footsteps of Ancient Pilgrims

Originally, the scenery was even more impressive than it is today: only 14 towers are left of the original 72. And all of the buildings you see were built within one short period, from 1200 to 1348, when the Black Plague hit the town and at least 50 percent of its population died.

In the aftermath of that catastrophe, a very weakened San Gimignano fell under Florentine rule and never fully recovered. For more than 500 years, the town was largely ignored by history – so when it was rediscovered by the budding tourism industry in the late 19th century, no modern activity had disfigured its ancient walls, its moment of brief medieval exuberance having been preserved like a fly in amber.

A tower in San Gimignano, New York of the Middle Ages"

Before leaving San Gimignano, make sure you visit the Historic Museum on Via Costarella where Michelangelo and Raffaello Rubino have recreated an authentic, built-to-scale (1:100) model of the Old Town. The exhibition is free and has been voted the no. 1 tourist attraction of San Gimignano.


We spent the night at the Relais La Costa Dimora Storica near Monteriggioni. This old pilgrims’ inn featuring guest rooms and stables for their horses had lain in ruins for centuries until Franco Vaselli got hold of it and turned it into a veritable Tuscan treasure.

We spent a single night there, but could have easily stretched that into a fortnight – sampling the many hiking trails in the area, spending lazy afternoons by the side of the swimming pool and enjoying the excellent food in the evenings.

On the way to the Relais – it is a little off the main road, and we had not seen any other car or any pedestrian for a good while – we were already wondering: where is the driver taking us? But then suddenly, a little like San Gimignano over the hills, a truly palatial residence appeared in front of us.

“When people tell me: this place is far away”, says Relais La Costa Dimora Storica’s General Manager Eglantina Ruko, “I always ask them: far away – from what?” And I must say that I could see her point.


It’s back to the Via Francigena and off to Monteriggioni Castle – in our next post!


Our trip to Tuscany was made possible on the invitation of the Council of Europe/European Commission Joint Programme 2013-2014 on European Cultural Routes, realized in co-operation with the European Institute of Cultural Routes(EICR).

Don’t miss our next post about our #FrancigenaTrip for the cultural #CrossingRoutes by following us on Facebook and Twitter. Better still, subscribe to our free updates via email.

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