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The hilltop towns of Tuscany were born in turbulent times – today, their medieval streets, churches filled with jewel-coloured frescoes and lofty views over the Tuscan countryside are the legacy of these rivalries.
Come during midweek and outside of the high summer season to beat the crowds at Unesco World Heritage Site Pienza, which owes its splendid Renaissance design to its favourite son, the 15th-century humanist Pope Pius II. The cathedral and old papal residence in the Palazzo Piccolomini stand on the town’s central square.
Built-upon narrow ridge Montepulciano is a test of leg muscles, but luckily the town’s famed Vino Nobile is always on hand for refreshment on the climb up the main street (Il Corso) to Piazza Grande at the highest point of the town. Gothic architecture is tempered with Renaissance grace, most notably at the Tempio di San Biagio. Built in the 16th century from pale golden stone, this church is the perfect expression of Renaissance ideals of geometry.
On a volcanic outcrop surrounded by gorges on three sides, Pitigliano looks as if it was grown rather than built. Twisting stairways disappear around corners, and cobbled alleys bend tantalisingly out of sight beneath graceful arches. The town is also nicknamed ‘Little Jerusalem’ as it was once home to the largest Jewish community in Italy. The old ghetto buildings survive, including a kosher butcher and a tiny, richly adorned synagogue.
Fifteen medieval towers give San Gimignano the appearance of a Tuscan Manhattan. In the town’s mid-14th-century heyday, there were as many as 72, built by wealthy local families trying to outdo each other. The town’s basilica, the Collegiata, is a riot of colourful frescoes by the likes of Taddeo di Bartolo, Benozzo Gozzoli and Domenico Ghirlandaio.
The well-preserved ramparts of the proud-looking town of Volterra offer views out as far as the Tyrrhenian Sea and the island of Corsica on a clear day. Volterra was a stronghold of the Etruscans before the rise of Ancient Rome, and the town’s Museo Etrusco Guarnacci has impressive exhibits on this lost civilisation, including an elongated bronze statue representing the silhouette of a naked man, entitled The Shadow of the Evening.
Once a stronghold for Florentines in their bitter wars with Siena, Castellina lies in the Chianti region – a wealthy area which is celebrated for its red wine. Highlights of Castellina include the atmospheric arched passageway of the Via delle Volte, and the Antica Fattoria la Castellina wine shop at Via Ferrucio 26, where you can sample the local vintages.
Despite WWII damage, Arezzo has photogenic streets and squares including the Piazza Grande, which holds a huge antiques fair on the first weekend of every month. Within the church of San Francesco, the Cappella Bacci displays a 15th-century fresco by Piero della Francesca – it remains one of the greatest works of Italian art.
Perched high even by Tuscan hill town standards, Cortona slopes down from the Fortezza Medicea – a ruined fortress with stupendous views across the plain below. The Museo Diocesano holds a couple of treasures, including two beautiful works by Fra’ Angelico, and the overhanging houses on Vicolo Ianelli are among Tuscany’s oldest.
High above the Arno River, Poppi Alta is the upper section of the town of Poppi, and is crowned by the narrow, 13th-century Castello dei Conti Guidi. Inside this castle there’s a dream-like courtyard, a handsome staircase, a library full of medieval manuscripts and a chapel with frescoes by Taddeo Gaddi (Piazza della Repubblica 1; closed Mon–Wed btwn Nov–Mar; admission £4).
Where to stay
Casa Chilenne is a welcoming, family owned b&b in a historic four-storey building inside Cortona’s old city walls, with five charming rooms, a small rooftop terrace and lavish breakfast spreads (Via Nazionale 65; from £90).
L’Antico Pozzo occupies a 15th-century building in San Gimignano, with high-ceilinged rooms and elegant décor. There’s an attractive breakfast room, and a summer courtyard (Via San Matteo 87; superior rooms from £130).
Luxury b&b La Locanda di San Francesco offers four lovely rooms in Montepulciano – two with magnificent views over the surrounding countryside (Piazza San Francesco 3; closed mid- Jan–mid-Feb; suites from £190).
BA, easyJet, Jet2.com and Ryanair fly to Pisa from UK airports including Gatwick, Stansted, Manchester, Edinburgh, Leeds and Bournemouth (from £85). For Florence, Meridiana flies from Gatwick (from £125) and CityJet departs from London City (from £130). Ryanair flies to Perugia in Umbria from Stansted (from £80). The best way to see all of Tuscany is by car (small cars from £130 per week), but on the small back roads, two wheels have their attractions (from £10 per day, scooters from £35 per day).