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Clement VII’s bastard son inherited the ducal mantle at 19, and soon became a despot, carousing with his cousin Lorenzino, who eventually grew jealous and murdered Alessandro.

Ambrogio Lorenzetti’s fresco of 1338 wraps around the medieval ruling Council of Nine’s inner chamber. Ruled by the allegorical figures of Good Government, medieval Siena prospers. Under Bad Government, it crumbles.

The last of the main Medici line. She willed all Medici possessions – including the collections in the Uffizi, Pitti and Bargello – to the Lorraine grand dukes on the stipulation the patrimony could never be removed from Florence.

The Antinori Marquises have been making wine since 1385, producing more than 15 million bottles annually of some of Italy’s most highly ranked and consistently lauded wines. You can sample their vini at Florence’s Cantinetta Antinori (see Cantinetta Antinori).

An Etruscan city, then ancient Roman pottery centre, Arezzo was later home to Guido Monaco, who invented modern musical notation in the 11th century, the poet Petrarch (1304–74) and Giorgio Vasari (1512–74), architect and author of the first art history text, Lives of the Artists .

The town’s centre is the broad, sloping Piazza Grande. The bell-tower, façade and medieval Calendar reliefs of the 12th-century Santa Maria della Pieve are Lombard-Romanesque style, but the altarpiece (1320) is pure Sienese Gothic courtesy of Pietro Loren-zetti. The Duomo has excellent stained-glass windows by French master Guillaume de Marcillat, and a fresco by Piero della Francesca. The 14th-century San Francesco is graced with Piero’s recently restored Legend of the True Cross (1448–66).

A 15-year restoration of the choir’s Legend of the True Cross (1448–66), the greatest fresco cycle by Piero della Francesca, has revived the vitality and vibrancy of this masterpiece.

Within its 14th-century walls, next to the travertine Romanesque Collegiata, Asciano’s Museo d’Arte Sacra contains Sienese works by Ambrogio Lorenzetti, Segna di Buonaventura and Francesco di Valdambrino. The minuscule Museo Etrusco’s 3rd- to 5th-century BC painted vases are installed in a deconsecrated church.

The Falvo brothers were key in reviving the quality and raising the status of Vino Nobile in the 1990s. The huge estate also produces vintages made with Merlot and Cabernet, and one of Tuscany’s finest Vin Santoe. A classy show-room/free tasting bar is in Montepulciano.

Little more than a square of houses around a vast, Medici-built portico and basin steaming with naturally carbonated, volcanically heated waters. St Catharine bathed here for her scrofula (lymphatic tuberculosis), Lorenzo the Magnificent for his troublesome arthritis, but sadly the pool is no longer suitable for swimming.

Massive American-owned estate founded in 1978, producing scientifically perfect wines and a massive Brunello riserva . There’s a huge shop and enoteca and a small glass and wine museum.