San Gimignano

San Gimignano grew rich in the 1200s on two things: saffron, which it traded widely, and traffic on the Via Francigena, the pilgrim road from northern Europe to Rome. Leading families showed off their money by building towers, each trying to outdo the next. At the peak there were about 72. A town law later said none could stand taller than the tower of the town hall.

The tallest survivor is the Torre Grossa, finished in 1311 and 54 metres high. It belongs to the Palazzo Comunale and is the one tower you can climb.

The Black Death of 1348 killed about half the people, and the town soon came under Florence. With no money to modernise, it was left almost as it was. That is why UNESCO listed the historic centre in 1990.

The local white wine, Vernaccia di San Gimignano, was the first Italian wine to be given DOC status, in 1966, and became a DOCG in 1993.

Most trips give you between one and a half and three hours inside the walls. Coaches park below the town, and you walk up through Porta San Giovanni on the south side. The main street climbs gently to Piazza della Cisterna, a triangular square around a 14th-century well. The gelato counters here draw queues all afternoon.

Next door is Piazza del Duomo. The Collegiata looks plain from outside, but the walls inside are covered with painted stories: the Old Testament on the left by Bartolo di Fredi, the New Testament on the right from the workshop of Simone Martini, and a Last Judgement over the door. The Santa Fina chapel has frescoes by Ghirlandaio.

The Torre Grossa is reached through the town museum in the Palazzo Comunale. The stairs are steep but short, and from the top you see the other towers and the hills toward Volterra.

On a wine day, expect a stop at a farm or cellar near the town to taste Vernaccia alongside Chianti reds, often with olive oil, cheese and salami. Longer itineraries pair San Gimignano with Siena, Volterra or Pisa, so the time in each place is shorter.

Timing matters more here than in a big city. The town is small, and between about 11:00 and 16:00 in high season the coach groups fill the two main squares and the gelato queue. Arrive early, or stay into the evening, and the same streets are close to empty.

April to June and September to October are the best months, with mild weather and green or golden hills. The grape harvest in the vineyards around the town usually runs through September, a good time for a wine-focused day.

Thursday and Saturday mornings bring markets to the squares. Winter is quiet and some shops close, but the town is at its most local. Summer afternoons can be hot on the stone streets, so carry water.