It was just after seven in the morning and Siena was still asleep. The hotel door clicked shut behind me and the street was entirely mine — no tour groups, no selfie sticks, no queue for the Duomo. Just wet tarmac, a grey February sky pressing down low on the hills, and the sound of my own breathing.
Looking back at Siena from the first rise — the city still half-hidden in the February murk. The olive trees were the only thing moving.
The route took me south almost immediately. A residential junction, ordinary Italian apartment blocks, and then a single flash of yellow mimosa — the only colour on the street that morning — bright against damp concrete like something that hadn’t read the forecast.
The junction at Ravacciano. The mimosa wasn’t there to impress anyone. That was the point.
And then the city just stopped.
One moment: suburban road, parked cars, a speed sign for 50. The next: vineyards rolling away to the horizon, olive groves banking down the hillsides, a stone farmhouse sitting alone on a ridge with a row of cypresses standing to attention. The kind of view you’ve seen in a thousand photographs, except you’re running through it in February drizzle and it is completely, stubbornly real.
The Malafrasca sign — and the crossed-out SIENA behind it. The moment the city ends and the countryside takes over.
Into the hills
The climb along the Strada dell’Ascarello is where it gets serious. The road rises steadily through the neighbourhood of Scacciapensieri — a word that translates, roughly, as chase away your worries — and the gradient earns its name. I stopped twice. Not because my legs needed a rest. Because the view back toward Siena demanded it.
Siena from the Scacciapensieri ridge. The Palazzo Pubblico tower just visible. Olive trees between you and it. No entry fee.
Tuscan hillside beyond the city boundary. Vines, olives, a farmhouse on the ridge. February makes the landscape honest — you see its bones.
Across the valley, the vines ran in clean geometric lines across the slope — bare in February, just wooden posts and wire and the shape of the land underneath. There’s something honest about vineyard rows in winter. Nothing to hide behind. The soil was dark with rain, the grass between the lines brilliantly green.
Strada dell’Ascarello looking south. The dirt track, the olives, the long view. Nothing between you and the horizon.
Down into the valley floor. Mud, posts, bare vines. The farmhouse on the ridge has been watching this field for longer than we can imagine.
Further out
Past the Malafrasca sign — past the point where Siena officially ends and the land takes over — the track drops into the valley and follows the edge of the vines. The views opened further. More hills, more cypresses in rows against the sky, more of that particular grey-green Tuscan palette that photography never quite captures accurately. We’ve tried.
Open country beyond Malafrasca. Olive groves and a cypress treeline. The kind of view that exists in people’s heads when they think of Tuscany, except quieter.
Looking back west toward the hills above Siena. The scale of it. The city tucked somewhere in the folds.
The way back
The return came through lanes I wouldn’t have found on a map. Narrow, hedged, with a farmhouse wall close enough to touch. Terracotta pots lined up outside a door — plants in them, cared for. Then a wide stone arch, a gate old enough to have a date carved into it, a column of cypresses rising behind it marking the entrance to something private and centuries old.
Stone arch gate on the return route. Cypresses behind it. Private estate — glimpsed from the road. Some things are better that way.
The narrow lane alongside the farmhouse wall. The potted plants outside the door. Someone’s ordinary morning.
Then the lane opened back onto tarmac, and the apartment blocks reappeared, and the large brick dome of a church rose above the treeline as the first marker that the city was close again.
The church that marked the edge of the city on the return. Brick dome, bell tower, cypress. Siena announces itself this way.
I made it back in just under fifty-five minutes. Seventh on a Strava segment I didn’t know existed — Ascarello ritorno — which felt like the right kind of minor victory for a February morning.
Siena was beginning to wake up.
5.95 mi · 54:58 · 551ft · 9:14/mi · 7th on Ascarello ritorno