GUBBIO is the most thoroughly medieval of the Umbrian towns, an immediately likable place that’s hanging onto its charm despite an ever-increasing influx of tourists. 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 commune, 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 – the reason it’s been spared the onslaught of the twentieth century and why getting here can be tricky.

Gubbio is easiest approached by bus from Città di Castello or Perugia on the lovely cross-country SS298 road . The nearest train station is at Fossato di Vico, 19km south on the Rome-Foligno-Ancona line; there are ten connecting shuttle buses to Gubbio from Monday to Saturday, six on Sundays.

The Town

Centre-stage is the immense and austere fourteenth-century Palazzo dei Consoli , whose crenellated outline and 98-metre campanile immediately grab your attention. Probably designed by Matteo Gattapone, who was also responsible for Spoleto’s Ponte delle Torri, the palace took a couple of hundred years to build and required the levelling of vast tracts of the medieval town, mainly to accommodate the huge and windswept Piazza della Signoria. The lesser Palazzo Pretorio opposite was built to the same plan. Deliberately dominating and humbling, it was what medieval civic pride was all about, an attempt to express power and supremacy in bricks and mortar. Behind a plain square deception (there’s a small hole top right where criminals were hung in a cage called la gogna – from vergogna or “shame”) is a cavernous baronial hall, the Salone dell’Arengo, where council officials and leading citizens met to discuss business. The word “harangue” derives from arengo , suggesting proceedings frequently boiled over.

The Museo Civico (Tues-Sun: April-Sept 10am-1pm & 3-6pm; Oct-March 10am-1pm & 2-5pm; L7000/¬3.62) is also based here, housing a typical miscellany, unremarkable except for the famous Eugubine Tablets (upstairs to the left), Umbria’s most important archeological find. Discovered in 1444 by an illiterate shepherd, later conned into swapping his priceless treasure trove for a worthless piece of land, the seven bronze tablets are more or less the only extant record of the ancient Umbrian language, a vernacular tongue without written characters. The bastardized Etruscan and Latin of their religious texts was aimed at producing a phonetic translation of the dialect using the main languages of the day. Gubbio was close to the shrine of the so-called Apennine Jove, a major pagan deity visited by pilgrims from all over Italy, so the tablets were probably the work of Roman and Etruscan priests taking advantage of the established order to impose their religious cults in a region where their languages weren’t understood. Most importantly, they suggest Romans, Etruscans and Umbrians achieved some sort of coexistence, refuting a long-held belief that succeeding civilizations wiped one another out.

Admission to the museum also gets you into the good five-roomed Pinacoteca upstairs, worth a look for works by the Gubbian School – one of central Italy’s earliest, and a collection of ponderous fourteenth-century furniture. Try the door at the back for views from the palace’s loggia . The palace also boasted 26 toilets; apparently it was the first in medieval Italy to have interior piped water.

To the north of the Piazza Grande lurks a not very inspiring thirteenth-century Duomo , partly redeemed by the odd fresco, twelfth-century stained glass, and some arches gracefully curved to emulate the meeting of hands in prayer. There are also a pair of carved organ lofts that for once don’t look as if they’d be more at home in a fairground. The small adjoining cathedral museum is currently closed after a spate of thefts, but if you’re lucky enough to find it open it’s well worth five minutes, mainly for a florid Flemish cope, presented to the cathedral by Pope Marcellus II, who was born in Gubbio.

The plain-faced Gothic pile is overshadowed by the Palazzo Ducale in Via Federico da Montefeltro opposite (Mon-Sat 9am-7pm, Sun 9am-1.30pm; closed first Mon of the month; L4000/¬2.07), built over an early Lombard palace by the Dukes of Montefeltro as a scaled-down copy of their more famous palace in Urbino. The courtyard is particularly good, and the interior, though stripped of most of its original furniture and other trappings, is now open after years of restoration and well worth the admission.

On the hillside above the town stands the Basilica of Sant’Ubaldo , a place Gubbians drive to for their Sunday-morning walk, but pleasant enough for that. There’s a very handy bar, plenty of shady spots to crash out, and some great views (even better ones if you can be bothered to climb up to the Rocca ). There’s not much to see in the basilica itself, except the body of the town’s patron saint, St Ubaldo, whose missing three fingers were hacked off by his manservant as a religious keepsake. You can’t miss the big wooden pillars ( ceri ) featured in Gubbio’s annual Corsa dei Ceri (May 15), little known outside Italy but second only to Siena’s Palio in terms of exuberance and bizarre pageantry. The rules and rigmarole of the 900-year-old ceremony are mind-boggling, but they boil down to three teams racing from Piazza della Signoria to the basilica, carrying the ceri (each representing a different saint) on wooden stretchers. By iron-clad tradition, the cero of St Ubaldo always wins, the other teams having to ensure they’re in the basilica before the doors are shut by the leaders. There’s hours of involved ritual at either end, vast crowds and plenty of drinking. A scholarly debate rages as to whether the whole thing’s intrinsically religious (commemorating the day in 1155 Ubaldo talked Barbarossa out of flattening Gubbio), or a hangover from some pagan fertility rite. Nowadays the Church, not surprisingly, claims it as its own, but judging by the very phallic ceri , and the roar that goes up when they’re raised to the vertical, there’s something more than belief at play here.

There are several ways up to the basilica, one being via the steep track that strikes off from behind the duomo. However, it’s quicker and far more fun – unless you have no head for heights – to take the funicular (summer 8.30am–7.30pm; winter reduced hours; return L9000/¬4.65, one way L7000/¬3.62) from Porta Romana, over on the orient side of town; you jump on small two-person cradles, which then hang precariously over the woods and crags below as you shudder slowly upwards. While you’re inactivity you could take in more of Ottaviano Nelli’s paintings, tucked away in the thirteenth-century Sant’Agostino and Santa Maria Nuova nearby. The unusually lovely Madonna del Belvedere (1408) in the latter is a masterpiece of the detailed and highly decorative style for which he was famous. His most majestic efforts – seventeen frescoes on the life of the Virgin – are in San Francesco , the big church that dominates the Piazza dei Quaranta Martiri – the bus terminal – at the foot of the town. The piazza’s titled in memory of forty citizens shot by the Germans in 1944, a reprisal for partisan attacks in the surrounding hills.

Gubbio’s Porte della Morte , the “doors of death”, are as controversial as the phallic ceri . Almost unique to the town (there are a few others in Assisi and southern France), these are narrow, bricked-up doorways wedged into the facades of its medieval townhouses (with the best examples in Via dei Consoli). The party line is that they were used to carry a coffin out of a house, and then having been tainted with death, were sealed up out of superstitious fear. Nice theory, and very Italian, but judging by the constricted stairways behind the doors, their purpose was probably defensive – the main door could be barricaded, leaving the more easily defended passageway as the only entrance.

There are dozens of picturesque odds and ends around the streets, which are as wonderfully explorable as any in the region. The Bargello in Via dei Consoli, the medieval police station, is worth tracking down and gives you the chance to survey the adjacent Fontana dei Matti (the “fountain of the mad”), otherwise undistinguished but for the tradition that anyone travel round it three times will wind up mad. There’s usually someone wondering whether to give it a go.