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St Francis himself founded this clifftop monastery, and a Baroque frescoed corridor passes the now-enclosed cave where he slept. At the end of the corridor is the Cappella delle Stimmate, which was built over the site where the saint received his stigmata in 1224. For a sense of the saint’s La Verna unencumbered by buildings, follow the path to Sasso Spico, another rocky outcrop where the holy man prayed.

Though Florence had already subjugated Pisa in the 16th century, Pisa’s silty harbour and unsure loyalties prompted Grand Duke Cosimo I to hire Buontalenti to build him a brand-new port from scratch. Livorno and Pisa have hated each other ever since.

Livorno is Tuscany’s second city, but short on sights when compared with, say, Pisa. There is just the somewhat wishfully named Venezia Nuova (“new Venice”) canal district, Pietro Tacca’s Mannerist masterpiece Monumento ai Quattro Mori (1623–6) at the port, and the Museo Civico Giovanni Fattori. The latter is devoted to native son Fattori, chief painter of the 19th-century Macchiaioli (Tuscan “impressionists”). Artist Amedeo Modigliani was also born here (but worked in Paris), as was composer Pietro Mascagni.

Elegant small city of avid cyclists, church concerts, Romanesque façades and exquisite Renaissance sculpture. Another one of Tuscany’s Top 10.

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).

Best suited to toddlers and small children, the courtyards of Europe’s oldest foundling hospital house a selection of toys. An adult must accompany your children.

Stay in one hotel or apartment and make day-trips. Changing hotels is a time-consuming hassle, and weekly rates are cheaper.

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.

This old mining town has a number of esoteric museums on the subject. Of particular artistic interest are the Dark Ages reliefs decorating the Romanesque Duomo. The Palazzo del Podestà houses a museum containing Ambrogio Lorenzetti’s Maestà (1330s) and a tiny pre-Etruscan menhir (flat stone carved vaguely as a person). The upper “new town” (developed in the 14th century) is defended by the Gothic Torre del Candeliere and ramparts, offering fine views over the town and Colline Metal-lifere (literally the “iron-rich hills”).

A natural sauna formed from a series of subterranean caves above a sulphurous underground lake, filled with hot mineral-laden vapours. (see Northwestern Tuscany)

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.