SAN GIMIGNANO, 27km northwest of Siena, is perhaps the most visited small village in Italy. Its stunning hilltop skyline of towers, built in aristocratic rivalry by the feuding nobles of the twelfth and thirteenth centuries, evokes the appearance of medieval Tuscany more than any other sight. And the town is all that it’s cracked up to be: quietly monumental, beautifully preserved, enticingly rural, and with a fine array of religious and secular frescoes. It takes around twenty minutes to walk from one end of town to the other, but it deserves at least a day, both for its frescoes and for its lovely surrounding countryside.

From Easter until October, San Gimignano has very little life of its own, with hordes of day-trippers traipsing up and down its narrow streets and filing in and out of its innumerable olive oil, wine and souvenir shops. If you want to reach beyond its facade of quaintness, try to come well out of season; if you can’t, then aim to spend the night here – the town takes on a very different pace and atmosphere in the evenings.

Brief history

In the early Middle Ages, San Gimignano was a force to be reckoned with. It was controlled by two great families – the Ardinghelli and the Salvucci – and its 15,000 population (twice the present number) prospered on agricultural holdings and its position on the Lombardy-to-Rome pilgrim route. At its peak, the town’s walls enclosed five monasteries, four hospitals, public baths and a brothel. Feuds, however, had long wrought havoc: the first Ardinghelli–Salvucci conflict erupted in 1246. Whenever the town itself was united, it picked fights with Volterra, Poggibonsi and other neighbours. These were halted only by the Black Death, which devastated first the population and then, as the pilgrim trade collapsed, the economy. Subjection to Florence broke the power of the nobles and so their tower-houses, symbolic in other towns of real control, were not torn down; today, fourteen of an original 72 survive.

Book through Rough Guides’ trusted travel partners

Italy features

The latest articles, galleries, quizzes and videos.

13 striking pictures of Venice Carnival

13 striking pictures of Venice Carnival

With the 2018 carnival season about to kick off, Rough Guides author and photographer, Kiki Deere, revisits one of Europe's most colourful festivals: Venice…

25 Jan 2018 • Kiki Deere insert_drive_file Article
20 picturesque Christmas destinations

20 picturesque Christmas destinations

Dreaming of a trip this Christmas? We're here to help. From glittering cities to a few snowy escapes, here are 20 classic destinations for a festive break. …

12 Dec 2017 • Rough Guides Editors camera_alt Gallery
Discovering Palermo: why you should give Sicily’s capital a chance

Discovering Palermo: why you should give Sicily’s capital a chance

A city of grit and forgotten grandeur, for too long Palermo has resigned itself to being a film set of crumbling palaces, sun-worn facades and pockmarked backst…

08 Dec 2017 • Olivia Rawes insert_drive_file Article
View more featureschevron_right