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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.

Alabaster-carving is the local speciality of this windswept town with its medieval alleyways. The Museo Etrusco Guarnacci has one of Italy’s finest Etruscan collections, and the worn basalt heads adorning Porta all’Arco (4th century BC) represent Etruscan gods. The remains of a Roman theatre and baths are best seen from the viewing point off Via Guarnacci. The Pisan-striped 13th-century Duomo, with its meticulously carved and painted ceiling, houses Byzantine and Renaissance treasures, while the Pinacoteca boasts a fully intact Taddeo di Bartolo altarpiece (1411), Ghirlandaio’s final painting (Apotheosis of Christ , 1492), Luca Signorelli’s Annunciation (1491) and Rosso Fiorentino’s masterful early Mannerist Deposition (1521).

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”).

The subject of the most popular aerial-shot postcard in Tuscany is a tiny hamlet two streets wide. It is entirely enclosed within medieval walls, whose 14 towers were compared by Dante to the Titans guarding the lowest level of Hell. The town holds a week-long medieval festival in July.

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).

Enter from the west to pass under Baccio d’Agnolo’s Mannerist Palazzo Campana gate (1539). The Duomo features a Giambologna/Pietro Tacca bronze crucifix and, in Mino da Fiesole’s tabernacle, a nail said to be from Christ’s cross. Palazzo Pretorio’s archaeological museum is most interesting for the 1920s political graffiti scrawled on this former prison’s inner walls by imprisoned Communists. The (intentionally) sgraffito-covered façade of Palazzo dei Priori hides a small museum of Sienese paintings.

Piazza Farinata degli Uberti is ringed by 12th- and 13th-century palaces and the Romanesque Sant’Andrea church. Collegiata di Sant’Andrea museum contains a Masolino Pietà (1425) and a 1447 font carved by Bernardo Rossellino. Masolino shows up again at Santo Stefano with a large Madonna and Child fresco; Rossellino with an Annunciation .

Frederick II built the imposing hilltop “Rocca” (great views) when this was the Tuscan stronghold of the German Holy Roman Emperors. The Duomo’s (rebuilt) Romanesque brick façade is studded with 13th-century North African majolica bowls.

Charming little brick town. Benozzo Gozzoli teamed with Giusto di Andrea on the Giustiziati tabernacle in Santi Michele e Jacopo church. Also inside, a 1503 bust and 1954 tombstone commemorate Decameron author Boccaccio (1313–75), who may have been born here; the Casa del Boccaccio, in which he passed his final years, is now a small museum and study library.

Santa Verdiana is Tuscany’s loveliest and most successful Baroque church. Its interior is swathed in frescoes celebrating the odd life of Verdiana, who walled herself into a cell here for 34 years with two snakes, which God sent to test her.