Cortona

Where it sits. Cortona clings to the southwestern flank of Monte Sant'Egidio in the province of Arezzo, at about 600 metres, looking out over the flat Valdichiana with Lake Trasimeno filling the horizon fifteen kilometres to the southeast. The position is the point of the place: every street either climbs or descends, the main square sits on the only substantial piece of level ground, and from the fortress at the top the view runs across two regions and, on a clear evening, as far as Monte Amiata. Umbria begins a few kilometres away, and Cortona has always felt like a border town facing outward rather than a Tuscan town facing Florence.

The story behind it. This was Curtun, one of the twelve cities of the Etruscan confederation, and the evidence is unavoidable: roughly three kilometres of massive polygonal walls still carry the medieval and modern town on their foundations, and the plain below holds monumental tumulus tombs — the Melone di Camucia and the two Meloni del Sodo — one of which was found in the 1990s to have a stepped ceremonial altar-terrace flanked by carved sphinxes. Rome absorbed the city, the Middle Ages fortified it, and in 1411 it was sold to Florence, after which it settled into a prosperous provincial existence. Hannibal destroyed a Roman army at Lake Trasimeno in 217 BC within sight of these walls.

What you actually see today. Piazza della Repubblica is the hinge of the town, dominated by the external staircase and clock tower of the Palazzo Comunale; Piazza Signorelli opens off it with the nineteenth-century Teatro Signorelli and the palace housing the MAEC. That museum grew out of the Accademia Etrusca, founded in 1727, and its two headline objects are an Etruscan bronze lamp of the fifth or fourth century BC — a heavy sixteen-nozzle chandelier covered in figures, weighing over fifty kilograms — and the Tabula Cortonensis, a bronze tablet found in 1992 carrying one of the longest Etruscan inscriptions known. The Museo Diocesano opposite the cathedral holds Fra Angelico's Annunciation, painted here around 1433, and works by Luca Signorelli, who was born in the town. The steep Via Santa Margherita climbs past mosaic Stations of the Cross made by the Futurist painter Gino Severini, another native son, to the basilica of Santa Margherita and then to the Medici Fortezza del Girifalco of 1556. Below the walls stands Santa Maria delle Grazie al Calcinaio, begun in 1485 to a design by Francesco di Giorgio Martini and one of the clearest Renaissance church interiors in Tuscany.

On screen. Under the Tuscan Sun (2003), directed by Audrey Wells and starring Diane Lane, is why a steady stream of American visitors has arrived here for two decades. It is loosely based on the 1996 memoir by Frances Mayes, who really did buy and restore a house near Cortona called Bramasole, on the road towards Torreone above the town. The film did not use it. The on-screen Bramasole is Villa Laura, a separate property in the countryside a few kilometres outside Cortona, chosen because Mayes had already finished restoring the real house and the story needed a ruin; Villa Laura was itself restored after the shoot by American owners and is now let to guests. Mayes's own house is private and not visitable, a distinction the tourist office spends a great deal of energy explaining. Town scenes were shot in Piazza della Repubblica, at the Teatro Signorelli and in the lanes around them, with other sequences filmed in Montepulciano, Florence, Positano and on the stages of Cinecittà in Rome — so the film's single Italian idyll is stitched together from places hundreds of kilometres apart. For contrast, Roberto Benigni shot Life Is Beautiful (1997) in Arezzo, thirty kilometres north, whose Piazza Grande carries that film rather than this one.

Food, wine and events. The Valdichiana below is the home of Chianina cattle, the enormous white breed behind bistecca alla fiorentina, and steak here is a local product rather than an import. Cortona has its own DOC covering Syrah in particular, which does unusually well on these slopes. Cortona On The Move, an international photography festival, takes over palaces and disused buildings across the town from summer into autumn and has become one of the more serious photographic events in Europe.

Getting there and timing. Two stations on the Florence–Rome line serve the town — Camucia-Cortona at the foot of the hill and Terontola-Cortona further south — with local buses climbing to Piazza Garibaldi; Florence is about ninety minutes away and Rome around two hours. Drivers should expect to park below the walls and walk up. The gradients inside are severe and the paving is stone, so this is a demanding town on foot. Late April to June and September to October are the best windows; summer afternoons on the exposed western slope are hot, but the same aspect makes for exceptional sunsets over the Valdichiana from the terrace outside the town walls.