Wine city
Known as the "Manhattan of the Middle Ages" for its iconic skyline of medieval towers, San Gimignano is a delightful hilltop town.
San Gimignano rises out of the hills of central Tuscany as a skyline of medieval stone towers — the "Manhattan of the Middle Ages" — about halfway between Florence and Siena. It is also a genuine wine town: the surrounding vineyards make Vernaccia di San Gimignano, a crisp, mineral white that in 1966 became the very first Italian wine to earn DOC status, and one of the first whites later raised to DOCG. After centuries as an afterthought to Tuscany's reds, Vernaccia is the reason to linger here beyond the towers.
The walled center is small and car-free, best explored on foot between the Collegiate Church, the two linked main squares and a climb up the Torre Grossa for the view over the vineyards. Wine estates ring the town within a few minutes' drive, many pouring Vernaccia alongside Chianti Colli Senesi reds and their own olive oil.
San Gimignano sits about an hour from Florence or 45 minutes from Siena and slots neatly into a Chianti or Val d'Orcia itinerary. Come in spring or early autumn to beat the day-tripper crowds that fill the lanes at midday in summer. Use the guide below to plan tastings in and around the town.