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The sweetest Casentino hill town, dominated by the Castello dei Conti Guidi (1274–1300), built by Lapo and Arnolfo di Cambio, the latter architect of Florence’s Palazzo Vecchio. Inside is a chapel, frescoed by Taddeo Gaddi.

Baratti Bay’s Iron Age role as port for Elba’s mines helped preserve Populonia’s Etruscan necropolis – under a slag heap. Half a dozen of the tombs are visitable, several almost intact. Museo Gasparri has many of the items excavated here.

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.

Michelozzo’s outside pulpit ensures that crowds in the piazza are able to see the bishop display the Virgin’s girdle (see Virgin’s Girdle (Prato, Duomo)). The graceful frescoes in the choir by Filippo Lippi include a famous scene of Salomé presenting Herod with the head of John the Baptist on a platter.

Took Perugino’s Umbrian style, and mixed it with Leonardo’s techniques and Michelangelo’s innovations to become supreme.

As Piero della Francesca’s heavy-lidded, heavily muscled Jesus rises from his sarcophagus, the dreary, dead landscape flowers into life (1463). The sleeping Roman soldier slumped in brown armour is said to be a self-portrait.

Early Baroque Flemish master who adapted Italian style to Northern tastes.

This massive, architecturally uninspired brick church of 1226 contains a portrait of St Catherine by her contemporary and friend Andrea Vanni. The saint’s mummified head and thumb are revered in a chapel decorated with frescoes on her life by Sodoma (1526) and Francesco Vanni. Matteo di Giovanni executed the saintly transept altarpieces.

The epitome of the perfect Italian hill town. The pride of this “Medieval Manhattan” is a group of 14 stone towers that seemingly sprout from the terracotta roof tiles. San Gimignano is surrounded by patchwork fields and vineyards producing Tuscany’s best DOCG white wine.

Best-preserved medieval hill town, complete with 14 stone towers (see San Gimignano).