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San Gimignano is a remarkable medieval town and UNESCO World Heritage Site, set on a particularly high hilltop in the Tuscan countryside. This fortified marvel is the historic equivalent of a modern high-rise city, with steel skyscrapers replaced with dizzyingly high ancient towers, and noisy alleyways swapped for uneven cobbled lanes.
The town’s 14 towers are a fraction of the 72 that once stood, but the impact is still impressive, with almost every square and street watched over by these soaring monoliths. For those with a head for heights, the tower tops offer unrivalled panoramas of the town’s winding lanes and the beautiful surrounding countryside. The 14th-century Torre Grosse is the best of these, and offers spectacular views from more than 170 feet above the streets. For those wanting to immerse themselves in history, the wonderfully tranquil Rocca de Montestaffoli is a must. This crumbling structure was once a fortress and a convent, although now it offers an atmospheric wild garden and one modest tower, with surprisingly good views over the countryside. If you’re in the mood for shopping, make sure you look out for some of the artisan workshops hidden in the town’s lanes – local photography and handmade ceramics are just some of the wares available.
The best thing to do in San Gimignano is the most obvious – scale a tower or two. Torre Grosse tops the Palazzo Comunale museum, while Torre e Casa Campatelli is part of a 19th-century noble’s house.
But some of the best views come courtesy of the Collegiate Church of San Gimignano. Make sure to admire the 14th-century frescoes before climbing the tower, which gives up valley views. Alternatively, head to San’Agostino Church. It doesn’t have a tower, but it does have a cloistered square.
Piazza della Cisterna is another must-see. This triangular market square is the liveliest spot in San Gimignano, stacking up gelato parlours and cafés.