Est. February 2026 · Dorset
RUNNER.KALICA

The Anglo-Italian Runner

Running · Photography · Europe Volume I · 66 routes logged

Walk San Gimignano, Tuscany · 12 February 2026

San Gimignano – Hilltop Village with the most amazing views.

Walk stats
3.47 Distance
1:36:24 Duration
320 ft Elevation
6,132 Steps
San Gimignano – Hilltop Village with the most amazing views.

San Gimignano requires a bus. Not because of any failure of ambition, but because the hill from Poggibonsi — where the train drops you, because San Gimignano has no station of its own — is the kind of gradient that makes you reconsider your whole approach to medieval hilltop towns. We’d already had a morning in Poggibonsi, which turned out to be considerably more than a place to change transport. That’s its own story. This one starts at the bus stop, at the foot of the walls, looking up.

The towers are visible before you get through the gate. That’s the point of them. Fourteen still standing out of what were once seventy-two — the medieval equivalent of a skyline flex, each one built taller than the last by competing families who apparently had strong feelings about being seen. Walking through the arch and into Via San Giovanni, you understand immediately why this place is on every list. It is also, in February, just about manageable.

The gate on Via San Giovanni. The town starts here. The towers start appearing immediately.

Via San Giovanni heading toward the centre. Medieval arches, stone and brick, a hotel sign as the only concession to the present.


The sandwich shop

Before the towers, before the piazzas, before any of the things San Gimignano is supposed to be about — there was the sandwich shop.

Da Noi Rosetta. Since 1700. The sign says so. The lady behind the counter — red bandana, focused entirely on the task — doesn’t look up when you come in. She’s at the slicer, working a joint of Mortadella Toscana with the kind of unhurried precision that makes you understand the sign is probably accurate. We watched. She sliced. She talked. She offered us the lard on a small piece of crust bread, pressed on us like a gift rather than a sample, with a look that suggested declining was not really an option.

We didn’t decline. We worked through the pickles and the chutneys and ended up with sandwiches that were, objectively, among the best things we ate in Tuscany. There was a photo outside the shop afterwards. Sarah has it. It’ll appear here when we get it. (For now: [link to their Instagram])

The kind of place that Sarah will absolutely be recommending on her Ravenna tours when they bring groups through Tuscany. The kind of place you find by wandering rather than searching.

Da Noi Rosetta, San Gimignano. The slicer, the Mortadella Toscana, the red bandana. Since 1700 — and you believe it.


The climb

San Gimignano is not flat. The Strava elevation tells part of it — 320 feet across 3.47 miles — but the real version is that it keeps going up, then drops sharply, then goes up again, and every time you think you’ve found the top there’s another alley that climbs. We went up and around the walls, out through a back gate, down a steep road that the route map shows as a tangle because we kept doubling back to look at things.

The views from the top are the reason for all of it. Olive trees and vineyards stretching out in every direction, terracotta rooftops in the foreground, the valley rolling away south toward Siena. In February the trees are silver-grey and the light comes and goes as the clouds move over. There was smoke from somewhere in the distance. It looked like a painting that a painter would probably have dismissed as too obvious.

From the walls, looking south. The valley, the olives, the smoke. February in Tuscany.


Three towers from the rooftop level. The sky doing the work. This is why they built them tall.


The wider view from the upper walls. Vineyards and hills as far as the light allows.


Piazza della Cisterna

The central piazza is herringbone brick, slightly sloped, with a medieval well in the middle and towers on two sides. In February it was close to empty. A delivery van was reversing somewhere off to the left. We stood there for a few minutes and said very little.

That’s San Gimignano working as intended.

Piazza della Cisterna. The well, the brick, the towers. February quiet.


The Duomo steps, Piazza del Duomo. The other piazza. Nearly empty.


Palazzo del Popolo and Torre Grossa. The civic heart of it. Two people walking through, which is about right.


The rainbow

We were heading back down toward the bus when it appeared. A double rainbow over the walls, catching the late afternoon light against the stone. Everyone in the car park stopped. Someone said something in Italian. Sarah must have taken 20 photos. I will get a better one from her later. We took the photograph, got on the bus, and talked about the sandwich all the way back to Poggibonsi.

Double rainbow over the walls of San Gimignano. The last thing we saw. The best thing.


San Gimignano, Tuscany – 3.47 miles – 1hr 36m – 320ft – 6,132 Steps (combined)