Montepulciano, Italy

The highest of the major Tuscan hill-towns, at more than 600m, MONTEPULCIANO is built on a long, narrow ridge 65km southeast of Siena, along which coils the main street, the Corso, flanked by a series of dark alleys that drop away to the walls, providing slivers of views between Renaissance palazzi out over the rolling countryside. Henry James, who compared the town to a ship, spent most of his time here drinking – a sound policy, in view of the much-celebrated Vino Nobile. A short distance east is the Etruscan-founded – but now rather drab – town of Chiusi, useful only as transport hub unless you're a devotee of Etruscan tombs and remains.