San Gimignano

Torre Grossa before the coaches, Piazza della Cisterna at dusk

One day is enough inside San Gimignano's walls. Arrive before the coaches to see the Collegiata frescoes and climb the Torre Grossa, spend midday at the Rocca di Montestaffoli and Sant'Agostino, and return to Piazza della Cisterna in the evening with a glass of Vernaccia as the towers catch the light.

Morning. Arrive early and walk in through Porta San Giovanni before the coaches. Head up Via San Giovanni to Piazza della Cisterna and Piazza del Duomo while they are still quiet, then go into the Collegiata for its walls of frescoes. Next door, buy the combined ticket for the Museo Civico and climb the Torre Grossa while the light is clear.

Midday. By late morning the main street fills, so move to the edges. Walk up to the Rocca di Montestaffoli for a free view over the rooftops and vineyards. Lunch in a side alley, or on the small square by Sant'Agostino, where the trattorias are calmer and cheaper.

Afternoon. See the fresco cycle of St Augustine's life inside Sant'Agostino, then follow the footpath outside the walls for countryside views. If you are curious about how the town looked at its peak, the SanGimignano1300 museum has a large model of the medieval town.

Evening. Come back to Piazza della Cisterna after the day groups leave, with a glass of Vernaccia, and watch the towers turn gold.

Vernaccia, saffron and pici with wild boar

San Gimignano's own wine is Vernaccia di San Gimignano, a dry white from the sandy hills around town, and its saffron flavours local pasta, cheese and ham. Order pici and wild boar, eat in the side alleys or near Sant'Agostino, and skip the tables with views over the main squares, which charge the most.

The local wine is Vernaccia di San Gimignano, a dry, slightly bitter white made from an old grape variety grown on the sandy hillsides around town. Order it by the glass with everything. Reds come from the wider Chianti area to the east.

San Gimignano has grown saffron since the Middle Ages, and it still flavours local pasta, sheep's cheese and a cured ham. Tuscan staples are everywhere: pici, a thick hand-rolled pasta, ribollita in the cooler months, and wild boar and other game. La Mangiatoia near Porta San Matteo serves game by candlelight, and Trattoria Chiribiri on Piazza della Madonna does simple homemade pasta (cash only).

Take the general rule seriously here: the restaurants with views over the main squares charge the most for the least. Eat in the side alleys or at places like the Locanda di Sant'Agostino, which fill with locals. The gelato shops on Piazza della Cisterna draw long queues all day. For a picnic, the Co-op supermarket sits by the car park below Porta San Giovanni.

Siena by direct bus, Volterra and Monteriggioni by car

Siena, about an hour away by direct bus, is the best day trip from San Gimignano. Volterra takes about two hours by bus with a change, so it suits drivers, as do Monteriggioni and Colle di Val d'Elsa. Florence is possible, but nearly two hours each way makes it better as a separate stay.

The town is small enough that one day inside the walls is plenty, so a second day is best spent in the surrounding Val d'Elsa.

Siena is the obvious choice, about an hour away by direct bus, with its shell-shaped Piazza del Campo and striped cathedral. Volterra, an Etruscan and medieval town known for alabaster carving, is about two hours by bus with a change in Colle di Val d'Elsa, so it works better with a car.

With wheels, the options widen. Monteriggioni, a tiny village inside a complete ring of walls and towers, sits beside the road to Siena. Colle di Val d'Elsa has a well-preserved upper town and a long glass-making tradition. The vineyards around San Gimignano itself are worth a tasting stop, since few Vernaccia producers export much.

Florence can be done as a day trip too, but the bus and train connections take most of two hours each way, so it is better treated as a separate stay.