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By carStefanoacetelli — CC BY-SA 3.0 (Wikimedia Commons)Siena, Italy · Italy
A whole valley listed as a World Heritage Site, and not for a monument: for the landscape its people created from the 14th century onwards, when Siena reorganised these hills to feed itself. The bare ridges, the lines of cypresses and the isolated farmhouses are not nature: they are a medieval design that survives almost intact. In the valley and on its edge, four villages that fit into four days and tell different stories: Pienza is the ideal city a Pope had built in one go, Montalcino lives off Brunello, Montepulciano, already on the watershed with the Valdichiana, off Vino Nobile, and Bagno Vignoni has a 16th-century thermal pool for a main square.
Down the Via Cassia · 53 km
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The natural starting point for the Val d'Orcia, fifty kilometres north. The Piazza del Campo, with its sloping shell shape, and the white and green marble Duomo are worth a morning before hitting the road.
Rent the car here rather than in Florence: you avoid the restricted traffic zone and a good hour on the expressway.
35 min to the next stop · 29 km
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A brick-walled village right on the Via Cassia, the road the Romans laid to head down to Rome. You cross it end to end in ten minutes, and it is the first sign you have left picture-postcard Tuscany behind.
Eat here before moving on: it is cheaper than in the valley villages and the cooking is the same.
20 min to the next stop · 18 km
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Etruscan in origin, it was one of the major stops on the Via Francigena, the medieval road linking Canterbury with Rome. It keeps the Collegiate Church of Saints Quiricus and Julietta, built over a temple from the year 714, and the Horti Leonini, a Renaissance garden open to the public.
This is your base for three days. It sits at the exact centre of the valley: nothing is more than half an hour away.
Montalcino and the southern valley · 80 km
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A 14th-century fortress dominates the village and the whole valley from above. But what made Montalcino famous across half the world is its wine: Brunello was born here, a long-aged red that was served to Queen Elizabeth II at a state dinner in 1969.
Climb up to the fortress and have a glass at the wine bar inside, in the parade ground. It is one of the few times a viewpoint and a cellar are the same place.
15 min to the next stop · 10 km
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A 12th-century Romanesque abbey built in a pale stone veined with alabaster, standing alone in a valley of olive groves. Legend credits it to Charlemagne. In the morning sun, the stone lightens and seems to glow.
Until 2015 the canons sang Gregorian chant here every day; check beforehand whether there is a sung Mass. Hearing it empty and in half-light is another thing entirely.
40 min to the next stop · 26 km
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Open-air hot springs, free and deep in the woods. The hot water has been depositing calcium carbonate for centuries and has built waterfalls of white stone; the largest is called the Balena Bianca, the white whale, for its shape.
Keep flip-flops and a towel in the car: there are no changing rooms or lockers. And go early in the afternoon, because it fills up later on.
Pienza and Montepulciano · 50 km
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This is where Enea Silvio Piccolomini was born, who became Pope as Pius II and decided to turn his home village into the ideal Renaissance city. He commissioned the square, the cathedral and the palace all at once, to a single plan. And then almost nothing changed for five centuries.
Try Pienza's pecorino, made from sheep's milk, at its different ages, from fresh to mature. And step onto the walk along the walls: it looks out over the whole valley.
15 min to the next stop · 10 km
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A tiny medieval village reached by a road lined with cypresses that is itself the picture of the Val d'Orcia. There is barely anything to visit inside: you come for the approach and the views.
Stop the car before you get there and walk the last stretch. The curve of cypresses is what you came to see, and you cannot take it in from the driver's seat.
20 min to the next stop · 8 km
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Just outside the valley, on the watershed with the Valdichiana, it is the largest village on this trip, strung along a long ridge. Its wine is the Vino Nobile, and you walk it by climbing the Corso from the gate to the main square, with the cellars dug out beneath the houses.
Look out from Piazza San Francesco: below, isolated among fields, stands the church of San Biagio, one of the purest Renaissance domes there is. And if you come in August, the Bravio delle Botti is a barrel race uphill.
The valley's most photographed corners · 35 km
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A tiny chapel with two cypresses beside it, alone on a low hill. There is no interior to visit and no opening hours: it is simply the image everyone has in their head when they say Tuscany.
You reach it by a dirt track off the San Quirico–Pienza road. At dawn, with mist in the valley, is when getting up early truly pays.
20 min to the next stop · 8 km
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A village where the main square is not a square: it is a 16th-century thermal pool, fifty metres long, steaming in the middle of the houses. The waters have been known since Roman times and both Saint Catherine of Siena and Lorenzo the Magnificent came here.
Nobody can bathe in the pool on the square. But go down to the Parco dei Mulini, where the water fell to the mills along a channel cut into the rock, and from there you see the valley.
10 min to the next stop · 4 km
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Two villages side by side beneath a medieval fortress visible from across the valley. The Rocca a Tentennano belonged to the Salimbeni, the family that rebelled against Siena, and from the top you understand why they built it there: it controls the whole pass.
It is the best viewpoint in the valley and almost nobody goes up. Walk the last stretch and save this for sunset, when the Val d'Orcia turns golden.
This getaway is in the app, day by day, with every stop on the map, the drives between them and where to sleep, and the option to save it for when there is no signal.
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