Seen from the surrounding countryside, San Gimignano looks like a medieval Manhattan: a cluster of stone towers rising from a hilltop above vineyards and olive groves in the Val d'Elsa. In its heyday, in the thirteenth and fourteenth centuries, the town had dozens of them, built by rival families as symbols of power and wealth. Fourteen survive, enough to make it one of the most recognisable towns in Italy and a UNESCO World Heritage site since 1990.
The town grew rich as a stop on the Via Francigena, the pilgrim route from Canterbury to Rome, and from the trade in saffron, which was grown in the area and sold across Europe. The plague of 1348 and the town's subsequent submission to Florence ended its golden age, and its decline froze it in time. The Collegiata, the main church, is covered inside with frescoes of Old and New Testament scenes, and the Palazzo Comunale and its tower, the Torre Grossa, can be climbed for a view over the rooftops and the hills. San Gimignano is also known for its white wine, Vernaccia di San Gimignano, which was the first Italian wine to receive the DOC designation in 1966. The town's gelato shops have a strong reputation, and the queues to prove it.
The centre is closed to traffic, and the town is crowded with day-trippers in summer, especially around midday. The best time to see it is early in the morning or in the evening, when the tour buses have gone and the towers glow in the low light. Park outside the walls in one of the car parks and walk in.
The riding around San Gimignano is classic Tuscany: winding roads through hills, past vineyards, cypress-lined drives and farmhouses. The roads toward Volterra, about thirty kilometres west, are particularly good, crossing a wilder landscape of rolling hills and clay badlands. To the east, Colle di Val d'Elsa, known for its crystal glass, and the Chianti roads beyond offer more curves.
Poggibonsi, about nine kilometres away, has fuel and every service. Spring and autumn are the best seasons for riding.