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Tiny, elliptical town, whose single street spirals to the 16th-century Collegiata church. Behind the church, the Palazzo Comunale houses a museum with late Gothic Sienese paintings and a 2m (6ft) high gold reliquary dubbed Tree of Lucignano (1350–1471).

The Frescobaldi Marquises, Tuscany’s largest private winemaking concern, have been viticulturalists for 30 generations (England’s Henry VIII kept some stock on hand). One of the first to experiment with non-native grapes (Pinots, Cabernet Sauvignon, Chardonnay, Merlot). You can visit several estates.

Not only did Masaccio imbue Renaissance painting with an unflinching naturalism, he also perfected single point perspective (Florence’s Santa Maria Novella’s Trinità ). Not the best draughtsman, but his strong brushstrokes and penetrating scenes are a cornerstone of Renaissance art.

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.

A split personality cathedral: Romanesque arcading topped by Gothic pinnacles and belltower. It houses wonderfully idiosyncratic sculpture: three takes on the life of local patron San Cerbone and lovely pre-Romanesque carvings.

Lorenzo the Magnificent recruited the young artist to study the sculptures in the Medici gardens.

Famously irascible, he was a sculptor of genius by his early 20s, who only painted the Sistine Chapel under protest. He also found time to design Florence’s defences, write quality sonnets and become a significant architect.

Full-bodied wines from the estate that was the first, in 1968, to make a single cru Chianti and a 100 percent Sangiovese Chianti.

The hometown of Tuscany’s mightiest wine, Brunello (see Brunello di Montalcino), is a small but proud burg, with an excellent wine shop in the ruined 14th-century Fortezza, a split-level main square and a lanky 1292 tower. The Museo Civico e Diocesano houses paintings by Simone Martini, Sano di Pietro and Vecchietta, and polychrome wood statues by Francesco di Valdambrino.

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.