Florence and the Tuscan hill towns — where the cypress-lined roads actually lead

Volterra — the oldest town in Tuscany

1h west of Florence by car, or bus via Colle Val d'Elsa (2h). Etruscan power center 2,800 years ago — before Rome existed. Etruscan Museum Guarnacci (€10): the "Shadow of the Evening" — thin bronze from 3rd century BC that looks like Giacometti. Roman theatre below town (€5). Alabaster workshops on Via Porta all'Arco — artisans carving for millennia.

Montepulciano & Pienza — wine and cheese

1.5h southeast of Florence. Montepulciano's Corso climbs to Piazza Grande lined with Renaissance palazzi. Vino Nobile di Montepulciano (DOCG, Sangiovese-based) — taste at Contucci's cantina beneath Palazzo Contucci (free, cellar from the 1500s). Pienza (15 min east): redesigned by Pope Pius II in 1459 as an "ideal city." Pecorino di Pienza aged in walnut leaves, ash, or grape must. View from Via dell'Amore over the entire Val d'Orcia.

Cortona — the Etruscan-to-English colony

30 min south of Arezzo. 600m above the Valdichiana plain. Museo dell'Accademia Etrusca (€10): 4th-century BC bronze chandelier. Fra Angelico's Annunciation in the Museo Diocesano (€5). Frances Mayes' "Under the Tuscan Sun" town — the actual house (Bramasole) is private. Trattorias where a three-course lunch costs €15.

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