San Gimignano from Orentano
~50 min by car Directions from Orentano
San Gimignano announces itself from miles away: a crown of medieval towers on a hilltop, the skyline that earned it the nickname "the Manhattan of the Middle Ages" and a UNESCO World Heritage listing.
Fourteen of the original seventy-odd towers still stand. Between them run two beautiful squares, the frescoed Collegiata, and shops pouring Vernaccia di San Gimignano — the town's own white wine, one of Italy's oldest named appellations.
Don't miss
- The towers — Climb Torre Grossa from the Palazzo Comunale for the classic view over the rooftops and vineyards.
- Piazza della Cisterna — The triangular square around a medieval well — the town's living room.
- Vernaccia — The local white wine, poured in every enoteca; the countryside around is full of tasting cellars.
Getting there
About 50 minutes by car from Orentano via the FI-PI-LI and Certaldo. Go early or late in high summer — the town is small and the day-tripper wave is real.
Back in the village by evening: see where to eat and what’s on tonight, or browse places to stay if Orentano isn’t your base yet.