San Gimignano

San Gimignano's skyline is medieval one-upmanship fossilised: its merchant families, grown rich on saffron and the Via Francigena pilgrim trade, built some seventy-two tower-houses in a contest of pure altitude, and the fourteen that survive still spike the hilltop like a Manhattan drawn in the thirteenth century. The town's luck was its misfortune - plague and Florentine takeover froze it before anyone could modernise, leaving streets, piazzas and towers essentially as the 1300s arranged them, which is exactly what UNESCO inscribed. Climb the Torre Grossa, the tallest at 54 metres, for the roofscape and the Val d'Elsa rolling away; the Collegiata's fresco cycles and the Palazzo Comunale's museum fill the culture card; and the Vernaccia di San Gimignano poured in every enoteca is one of Italy's oldest named white wines, local pride in a glass.

What you actually see

• The towers from Piazza della Cisterna - the full medieval skyline overhead.
• Torre Grossa - the 54-metre climb to the roofs and the Val d'Elsa.
• The Collegiata frescoes - biblical cycles lining the Romanesque cathedral.
• Vernaccia in an enoteca - the town's ancient white wine with a tower view.

When to go

Spring and autumn for walking weather; come before 10 or after 17 in any season, because the day-trip wave from Florence and Siena owns the middle hours. Evening, when the coaches leave, returns the town to its residents and the light goes honey-coloured.

Honest expectations

This is one of Tuscany's most visited small towns and the main street is a corridor of souvenir and food shops - the magic lives early, late and in the side lanes. Parking sits below the walls with a climb up. The famous gelato queues are long; the gelato is genuinely good.

Nearby

Volterra half an hour west, Certaldo below, and both Florence and Siena within easy reach.