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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.

This roofless 13th-century abbey and unique domed chapel on the hillside above are associated with the legend of a 12th-century soldier who plunged his sword into a stone to mark the end of his warrior ways.

Ambrogio Lorenzetti frescoes (1344) illustrate the holy vision that triggered the incident (see Miracles and Relics).

The ultimate hill town ranks second among Tuscany’s overall Top 10 for its remarkable medieval stone “skyscrapers”, fine white wine and gorgeous Gothic frescoes.

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.

A medieval fairy-tale town with stone towers and churches swathed in frescoes, surrounded by patchwork fields and terraced vineyards.

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

The Town of Towers looks as Tolkeinesque as they come, a medieval fairy-tale city full of towers to climb, alleys to explore and a half-ruined fortress to clamber about. The torture museum stuffed with gruesome instruments also appeals to children.

The “Medieval Manhattan’s” main church is covered inside with 14th- and 15th-century frescoes, including a cycle by Ghirlandaio in the Chapel of St Fina. (see Collegiata)

San Lorenzo was the Medici parish church. The family tombs are decorated by Donatello, Rosso Fiorentino, Bronzino and Filippo Lippi, with architecture by Brunelleschi (interior and Old Sacristy) and Michelangelo (Laurentian Library and New Sacristy). The New Sacristy contains Michelangelo’s roughly finished Dawn, Dusk, Day and Night .

A famous outdoor market offering leather goods, fashion items and marbled paper. The adjacent food market is open every morning except Sunday.