---
title: The Long Climb to Montalcino
date: '2025-09-06 20:00'
location_name: Montalcino
location_country: Italy
lat: 43.058
lng: 11.489
hero_image: hero.jpg
hero_alt: Hairpin road climbing through olive groves towards a hilltop town
published: true
---
The profile showed fourteen kilometres at an average of six percent. In practice it was steeper at the bottom and gentler at the top, which is the worst possible arrangement. We started climbing at two in the afternoon, which was also the worst possible decision.

[scrolly-section image="hero.jpg" alt="Empty road rising steeply through olive groves" caption="SP55 — 14km, 840m elevation gain"]
The first kilometre is the most honest. You find out immediately whether your legs have anything to say.

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By the halfway point the olive groves had given way to scrub oak and the road had narrowed to a single lane. No cars had passed in forty minutes. The silence was absolute except for breathing.

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Then, at the last bend before the top, the town appeared. Just the outline of it — a tower, a wall, rooftops. It was enough.
[/scrolly-section]

[chapter-break image="photo.jpg" title="Montalcino" number="II" alt="Medieval town gate with stone archway" /]

[pull-quote image="photo.jpg" alt="Rows of Brunello vines descending from hilltop town"]
From the top you could see the whole valley we had spent two days riding through. It looked completely flat from up here.
[/pull-quote]

We found a bar in the main piazza. The owner brought two glasses of water without being asked. Then two more. Then a small plate of bread and oil that nobody ordered. We sat there for an hour.

[scrolly-section image="photo.jpg" alt="Shaded medieval piazza with stone buildings" caption="Piazza del Popolo, Montalcino"]
The piazza at five in the afternoon is a different place from the piazza at noon. People have returned from wherever they go during the heat.

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A wine shop with barrels in the window and a handwritten list on a chalkboard. We looked at it for a long time and bought nothing. The prices were very reasonable and this felt suspicious.

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A cat on a warm stone wall, watching traffic that did not exist. It had clearly been watching this traffic for years.

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The fortress walls turn amber just before sunset. You could photograph this from a hundred different angles and it would look the same in all of them: very good.

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The descent back to the valley takes twenty minutes. The climb took two and a half hours. This ratio never stops feeling wrong.
[/scrolly-section]

We found the agriturismo by following a handwritten sign nailed to a cypress tree. It was exactly what it promised to be.
