Gubbio, Italy

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.

A powerful medieval Comune, and always important as the gateway to Ravenna and the Adriatic (it was a key point on the Roman Via Flaminia), these days it's a town apart, not really part of Umbria, Tuscany or Marche – one reason it's been spared the onslaught of modernity.