Medieval Villages · ~45 min from Chianti
San Gimignano:
the Manhattan of the Middle Ages
Fourteen medieval towers rise into the sky like skyscrapers from another age: San Gimignano has one of Italy's most iconic skylines and is one of Europe's loveliest small towns. A UNESCO World Heritage Site since 1990, this town on the Via Francigena has preserved its medieval layout. Seen from outside at sunset, its towers glowing pink against the Tuscan sky, it is a sight that stays with you.
The towers: symbols of power
In the Middle Ages, San Gimignano's noble families competed to build the tallest tower as a sign of prestige and power. At their peak there were 72 towers. Today, 14 remain, including Torre Grossa, the tallest at 54 metres, which is open to visitors. Climb it for a 360-degree view of the hills around Siena that looks almost like a painting.
💡 Timing your visit
San Gimignano is very popular in summer, especially at weekends. Arrive by 9:00 or after 17:00 for a quieter visit. On weekdays in spring and autumn, the town feels more intimate and its local character comes to the fore.
Vernaccia di San Gimignano
San Gimignano is also the home of Vernaccia, the first Italian wine to receive DOC status in 1966. White and dry, with notes of white flowers and almond, it is lovely as an aperitif or with freshwater fish. The Wine Museum in Piazza della Cisterna offers guided tastings in a remarkable historic setting.
World-champion gelato
Gelateria Dondoli in Piazza della Cisterna has won the Gelato World Championship three times. Vernaccia gelato with pine nuts and Roquefort, or the saffron-flavoured Crema di Santa Fina, are distinctive flavours you will struggle to find elsewhere. The queue is long, but every minute is worth it.
- Piazza della Cisterna — The lively heart of the town, with its medieval well at the centre
- Collegiata di Santa Maria Assunta — Beautiful frescoes by Ghirlandaio and Bartolo di Fredi
- Rocca di Montestaffoli — The remains of the fortress, offering another panoramic viewpoint
- Museo Civico — Masterpieces of medieval art from Siena and Florence
"San Gimignano is one of those places that makes you believe time really can stand still."
What to eat
The local food reflects the farming traditions of the Val d'Elsa: homemade pasta, wild boar stew, pecorino cheeses and artisan cured meats. Look for trattorias away from the busiest streets of the historic centre for more modest prices and traditional cooking.