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A walk around Tuscany's medieval Manhattan

Mint Mumbai

|

July 18, 2025

San Gimignano has close to 15 medieval towers, which were erected by wealthy families as status symbols

- Anita Rao Kashi

A walk around Tuscany's medieval Manhattan

Driving through Tuscany's fertile plains speckled with bales of hay, rolling vineyards and scattered hills, feels like stepping into the film Under The Tuscan Sun. The roads are relatively less crowded. Little villages and towns pop up and recede regularly. In the midst of all this, one hill stands out, with stone walls running along the edge, houses perched on the side and a number of towers making up the skyline. In the early morning sunlight, everything is doused in a golden glow. Even from afar, the Italian town of San Gimignano is arresting.

The day starts out without a plan. Eager to ditch the heaving crowds of Florence, an aimless drive through Tuscany sounds good. But road signs to San Gimignano and the eventual glimpse of the hill town are compelling enough for us to head towards it. A winding road leads up to the town's outskirts, from where visitors are encouraged to go on foot and with good reason. Walking into town through the Porta San Giovanni, the town's southern gate, is like stepping through a portal into the past. The first impression is of cobblestone paths, arched doorways and narrow alleys with ancient buildings and pretty houses sitting cheek by jowl.

It is still early on a weekday morning and there are just a handful of locals heading purposefully to their destinations. Gentle breeze carries the smell of freshly-baked bread and coffee from bakeries and cafés.

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