In the thirteenth century San Gimignano's families competed at building tallest: seventy-two towers, a contest of pride in stone. Thirteen survive, enough to make the town the "Medieval Manhattan", UNESCO-listed since 1990: nowhere else preserves so intact the skyline of a merchant city of the 1200s, grown rich on Via Francigena pilgrims and saffron.
What to see
Piazza della Cisterna with its well and Piazza del Duomo, the two connected drawing rooms; the Collegiata with Ghirlandaio's frescoes in Santa Fina's chapel; and the Torre Grossa, the only climbable tower: fifty-four metres of stairs and the whole Val d'Elsa at the top. In the Civic Museum, Lippo Memmi's Maestà stands up to Siena's.
Visiting
The town takes half a day, but it is in late afternoon — coaches gone — that it becomes its own again. Combined tickets cover museums and tower; Vernaccia di San Gimignano, the first Italian wine granted DOC status in 1966, is tasted in wine shops overlooking the very hills that raise it.
Getting there
By car from Florence or Siena (under an hour), car parks outside the walls and a walk up. By public transport: train to Poggibonsi, then a twenty-minute bus. The Francigena, for walkers, remains the noblest entrance.
Our editors' tip
Sleep inside the walls: San Gimignano at dawn and after dinner, lanes empty and towers floodlit, is another town from the eleven-o'clock one. And the prize-winning gelato on Piazza della Cisterna is no legend: the queue moves fast and the saffron cream is a local manifesto.