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Siena may have grown to small city size, but it retains a homey, hill-town atmosphere. Its travertine-accented brick palaces, stone towers and fabulously decorated churches are strung along three high ridges at the south end of the Chianti hills. (see Siena’s Duomo)

The epitome of the perfect Italian hill town. The pride of this “Medieval Manhattan” is a group of 14 stone towers that seemingly sprout from the terracotta roof tiles. San Gimignano is surrounded by patchwork fields and vineyards producing Tuscany’s best DOCG white wine.

The world’s greatest alabaster craftsmen inhabit the loftiest hill town in Tuscany, whose stony medieval streets rise a cloud-scraping 555 m (1,820 ft) above the valley. This was one of the key cities in the Etruscan Dodecapolis confederation (see Etruscan Sights Around Cortona). The museum (see Volterra’s Museo Etrusco Guarnacci) is filled with finds unearthed as the erosion that is affecting one end of town slowly exposes ancient tombs.

The town rises from a Medici city gate to the hilltop Piazza Grande with its crenellated Michelozzo-designed Palazzo Comunale and brick-façaded Duomo. Along the way, the main street passes Renaissance palaces, 19th-century cafés and dozens of wine shops where the samples of grappa and Vino Nobile (see Wine Houses) flow freely. You can also visit the cellars beneath the town.

This Etruscan settlement above the Chiana Valley is a trove of ancient tombs and Renaissance art. Stony buildings, steep streets and interlocked piazze characterize the centre. The upper half of Cortona has a sanctuary, the 16th-century Medici fortress, numerous gardens and little-known lookouts.

Montalcino stands proudly high above the valley; this was the last ally of Siena against Florentine rule. The hilltop eyrie is dominated by the shell of a 14th-century fortress, which has fantastic views, and is now a place where you can sample Montalcino’s Brunello wine (see Tuscan Wine Styles), Tuscany’s most robust red.

Italy’s only perfectly planned Renaissance town centre was commissioned from Rossellino by Pope Pius II. The perimeter street offers views over the rumpled green, sheep-dotted landscape. The town’s many little shops specialize in Tuscan wines, honey and the best pecorino sheep’s milk cheese in all of Italy.

Two hill towns in one. The “Old Town” centres on a triangular piazza with the Duomo and the crenellated mayor’s palazzo (a museum of local antiquities and Ambrogio Lorenzetti’s Maestà ). The upper “New Town” was founded in the 14th century by the conquering Sienese. Their fortress offers sweeping views over the hills.

In the heart of the Etruscan Maremma, surrounded by valleys full of ancient tombs, Pitigliano is built upon an outcrop of tufa rock. In fact, it is difficult to tell where the cliff sides end – pockmarked as they are with cellar windows – and the walls of the houses and castle begin.

Fiesole was the hilltop town that Roman Fiorentina was built to compete with. The town has a Roman theatre, small museums of art and archaeology, cool summertime breezes and views across to Florence.