HILL TOWNS
1. Cortona
This Etruscan settlement (see Cortona) 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 town has the Sanctuary of St Margaret, the 16th-century Medici fortress and little-known lookouts.
Town hall, Cortona
2. Siena
Siena may have grown to small city size (see Siena’s Duomo), but it retains a homey, hill-town atmosphere (see Siena). 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.
3. Volterra
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 Volterra: Museo Etrusco Guarnacci). The museum (see Florence’s Museo Galileo) is filled with finds unearthed as the erosion that is affecting one end of town slowly exposes ancient tombs.
4. Pienza
Italy’s only perfectly planned, Pienza Renaissance town centre (see Pienza) was commissioned from Rossellino by Pope Pius II in the 15th century. The perimeter street offers views over the rumpled green, sheep-dotted landscape. The town’s shops specialize in Tuscan wines, honey and the best pecorino sheep’s milk cheese in all of Italy.
Pienza pecorino
5. San Gimignano
This medieval Manhattan – a UNESCO World Heritage Site and the epitome of the perfect Italian hill town – boasts 14 stone towers of varying heights (the tallest 54 m/177 ft) that seem to sprout from the terracotta roof tiles. The town (see San Gimignano) is surrounded by patchwork fields and vineyards that produce Tuscany’s best DOCG white wine (see San Gimignano).
6. Montepulciano
From the Medici city gate to the hilltop Piazza Grande with its crenellated Michelozzo-designed Palazzo Comunale and brick-façaded Duomo, the main street passes palazzi, 19th-century cafés and wine shops where the samples of grappa and Vino Nobile (see Avignonesi (Montepulciano)) flow freely. You can also visit the cellars beneath the town (see Montepulciano).
Montepulciano, with Tempio di San Biagio church in the foreground
7. Montalcino
Montalcino stands proudly high above the valley; this was Siena’s last ally against Florentine rule. The hilltop eyrie is dominated by the shell of a 14th-century fortress with fantastic views, and is now a place where you can sample Montalcino’s Brunello wine (see Banfi (Montalcino)), wine, the region’s most robust red.
8. Massa Marittima
The Old Town (see Massa Marittima) centres on a triangular piazza with the Duomo and the crenellated mayor’s palazzo. The upper New Town was founded in the 14th century by the conquering Sienese, whose fortress now offers visitors sweeping hill views. The Museum of Sacred Art in the museum complex of San Pietro all’Orto holds Ambrogio Lorenzetti’s Maestà.
9. Pitigliano
In the heart of the Alta Maremma, surrounded by valleys full of old tombs, Pitigliano is home to a historically important Jewish community. It 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.
The clifftop town of Pitigliano
10. Fiesole
Roman Florentia was built to compete with this hilltop town (see Fiesole). Fiesole has archaeology and art museums, a Roman theatre, cool summertime breezes and views across to Florence.
