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The estate that invented modern Chianti Classico is back in the Ricasoli family after years under Seagram’s, and the wines have improved vastly. “Iron Baron” Bettino Ricasoli, Italy’s second prime minister, perfected the formula here.

Off Piazza del Municipio, Sant’Agostino has a trove of paintings, starring the 13th-century St Francis by Margheritone d’Arezzo, Gaddi’s Madonna and Child and Bartolomeo della Gatta’s St Francis Receiving the Stigmata .

This charterhouse, home to Carthusian monks from the 1300s to 1956, now serves the Cistercian Order. The building retains an original small monk’s church, a visitable cell and peaceful Renaissance cloisters set with della Robbia terracotta tondi and a small gallery of the Pontormo frescoes (1523–5).

Tuscany’s famous wine region has vineyards and castles, market towns and monasteries.

The fine Museo Archeologico Nationale Etrusco in Chiusi contains bucchero (black Etruscan earthenware), bronzes, anthropomorphic canopic jars and even a few 2nd-century BC painted funerary urns. Apply here to visit the best decorated tombs in the valley.

The 12th-century Duomo is swathed in trompe-l’oeil frescoes (1887–94) that look like medieval mosaics. Next door, the Museo della Cattedrale preserves 15th-century illuminated scores from Monte Oliveto Maggiore. Meet here for guided visits to the Etruscan-carved “Labirinto di Porsenna” tunnels.

Cortona is the quintessential Tuscan hill town with its Etruscan tombs, medieval alleys, Renaissance art and excellent restaurants.

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.

The first Medici to gain the title grand duke was created Duke at the age of 17, when the first primary Medici line petered out. He conquered Siena, built a port (Livorno) and ruled judiciously but with something of an iron fist.

Adroitly managed his family fortune, political clout and personal image to become the de facto ruler of Florence. Each time he was exiled or imprisoned by rivals, popular sentiment brought him back to power.

At the age of 26, Michelangelo took on a huge slab of marble, nicknamed “the Giant” by the sculptors of the day, and turned it into David (1501–4), an intense young man contemplating his task as a proper Renaissance humanist would. Intended for Florence’s Duomo, it first stood in front of the Palazzo Vecchio, was damaged during an anti-Medici riot, and eventually wheeled to the Accademia for safekeeping.