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Most beloved of the Medici. A devout humanist and patron of the arts (and a fair poet himself) who, alongside many accomplishments of his own, sponsored Michelangelo’s early career. Able ruler of the city.

An elegant city of opera and arcaded Romanesque façades. The medieval towers and 16th-century ramparts are now domesticated as small parks.

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

San Martino is a masterpiece of Romanesque stacked open arcades, stuffed with sculpture from Gothic reliefs to works by two great 15th-century talents, local Matteo Civitale and Sienese Jacopo della Quercia. (see Lucca)

Excellent deli with fine cheeses and meats. The nearby grocer sells wine and packaged regional foods.

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.

Tiny, popular trattoria in the town centre, where you can try pinci in wild boar sauce and veal with forest-picked asparagus.

Though predominantly 15th century, bits of the palazzo date back to times when it hosted, variously, Dante and Inquisition trials. Large rooms and iron bedframes lend an antique air, and “superior” rooms come with 17th-century frescoes.

This pastry and panino wine bar occupies an airy medieval room. Don’t miss the deli counter at the back.