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

This hilltop Etruscan settlement is a short ride from Florence on a No. 7 bus. The 11th-century cathedral was assembled using ancient Roman columns, and houses Renaissance sculptures by Giovanni della Robbia and Mino da Fiesole. The remains of a Roman theatre and baths are still used for summer concerts. The steep road up to San Francesco church, with its quiet cloisters and quirky missionary museum, passes a popular park, shaded by ilex and peppered with water-colourists reproducing its famous view of Florence.

The mercantile tradition of this fast-growing city dates to 15th-century financial genius Francesco Daitini, famed “Merchant of Prato” and inventor of the promissory note. His frescoed Palazzo is one of the best preserved of its kind in Italy. Prato’s best art decorates the Duomo (see Prato’s Duomo), but the Galleria Communale has a lovely collection of early Renaissance polyptych altarpieces by such masters as Filippo Lippi and Bernardo Daddi. The half-ruined Castello dell’Imperatore (1420s), its ramparts and grassy interior now a city park, was built by Emperor Frederick II to defend the road from his German kingdom home to his lands in southern Italy.

An ancient Roman town of metal workers – the industry’s thin daggers, which evolved into handguns, were called pistole after the city. It is an artistic crossroads where the striking Romanesque stripes in San Giovanni Fuoricivitas and the Duomo (see Pistoia’s Duomo) meet the Florentine Renaissance glazed terracottas festooning the Ospedale del Ceppo. Gothic art comes in the form of colourful 1372 frescoes covering the Cappella del Tau, and a Giovanni Pisano carved pulpit (1298–1301) in the church of Sant’Andrea.

This most decorous of Medici mansions became a model for the ultimate Renaissance villa; it was designed by Giuliano da Sangallo and frescoed by the likes of Filippino Lippi and Pontormo.

Medieval capital of the Mugello region, surrounded by Medici villas such as Cafaggiolo (see Villa di Cafaggiolo) and the Michelozzo-designed Castello del Trebbio (1461). In the town itself, painstakingly rebuilt after a 1919 earthquake, the 12th-century Pieve di San Lorenzo contains Renaissance altarpieces by Taddeo Gaddi and Bachiacca, apse murals by local Art Nouveau ceramics entrepreneur Galileo Chini (1906) and a damaged Madonna fresco by Giotto.

The mansion is gone, but Buontalenti’s fountain-filled and statue-studded Pratolino park remains a favourite excursion from Florence.

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).

In 1452, on the outskirts of this unassuming medieval hill town, a bastard child was born named Leonardo, who grew up to become one of the greatest scientific minds and artistic talents in history. The 11th-century Castello Guidi now houses a Museo Vinciano devoted to over 100 models of the master’s inventions. Up the road, set in an olive-clad farmscape that might have come from one of his works, is Leonardo’s simple casa natale (birthplace).

Terracotta-producing town with a miracle-heavy Renaissance Collegiata church. Flanking the high altar are chapels designed by Michelozzo and decorated with Luca della Robbia terracottas. The right one contains a fragment of the True Cross, the left an icon of the Virgin (supposedly painted by St Luke), which was buried here during the early Christian persecutions and ploughed up by an ox while the church foundations were being dug. Also on view are fine Baroque paintings and a Mannerist Giambologna crucifix.