GUBBIO is the most thoroughly medieval of the Umbrian towns, an immediately likeable place that’s hung on to its charm despite an ever-increasing influx of visitors. The streets are picture-book pretty, with houses of rosy-pink stone and seas of orange-tiled roofs; the setting is equally gorgeous with the forest-clad mountains of the Apennines rearing up behind. A broad and largely unspoilt plain stretches out in front of the town, and the whole ensemble – especially on grey, windswept days – maintains Gubbio’s tough, mountain-outpost atmosphere.
The town was once a powerful medieval comune, always important as the gateway to Ravenna and the Adriatic (it was a key point on the Roman Via Flaminia), but these days Gubbio is a town apart, not really part of Umbria, Tuscany or Le Marche – one reason it’s been spared the onslaught of modernity. Buses arrive in the Piazza dei Quaranta Martiri at the foot of town, named in memory of forty citizens shot by the Germans in 1944, a reprisal for partisan attacks in the surrounding hills. It’s a ten-minute walk uphill from here to the central Piazza Grande and Gubbio’s main sights.