A route of about 300 km crossing the Chianti, the Val d’Orcia and the Maremma. No motorways, no hurry. Just road
The Route
There is no right starting point for this weekend — there is only the moment you decide to go. But if you want a reference point, start from Siena. From there, everything else follows naturally.
Total km: approximately 300 km Duration: 2 days Difficulty: easy — no challenging passes, roads in good condition Best period: April-May, September-October
Day 1 — From Chianti to Val d’Orcia
Siena → Radda in Chianti (35 km)
Leave Siena heading north and take the Chiantigiana immediately — the SR222. It’s no secret, I know. But there’s a reason everyone knows it: it works. The vineyards flow on either side, the bends are wide and fluid, the tarmac is good. Don’t go fast. There’s no point going fast here.
Stop in Radda. Order something at the bar in the square. Watch the people passing by.
Radda in Chianti → Montalcino (80 km)
Here you leave the Chiantigiana and start heading south on roads that most tourists don’t know. Pass through Castelnuovo Berardenga, then descend towards Buonconvento along the SR2 — the ancient Via Cassia. It’s a straight road, but the landscape is that of the Sienese crete: bare hills, clay, a silence you can see.
From Buonconvento climb towards Montalcino. The arrival from the north offers a view of the village that alone is worth the journey.
Lunch in Montalcino. Something simple — pici al ragù, if you can find them. A glass of Rosso di Montalcino, not the Brunello — not today, you’re on a motorcycle.
Montalcino → Bagno Vignoni (25 km)
Twenty minutes of road, but don’t rush it. Descend towards San Quirico d’Orcia through the hills of the Val d’Orcia. If you’re lucky with the afternoon light, you’ll stop ten times just to look.
Bagno Vignoni is not a normal village — at the centre of the square there is a medieval thermal pool instead of a fountain. Park the bike, walk around, don’t quite understand what you’re looking at, then understand everything.
Sleep in San Quirico d’Orcia or nearby. An agriturismo if you can — it’s worth it.
Day 2 — Val d’Orcia and Maremma
San Quirico d’Orcia → Pitigliano (90 km)
Morning is the best time in the Val d’Orcia. Leave early, when the light is still low and the shadows are long.
Head down towards Piancastagnaio passing by Amiata — don’t go to the summit, that’s not this trip. But the loop around the foot of the volcano on narrow roads through chestnut trees is one of those stretches you will remember. Then descend towards the Maremma.
Pitigliano appears suddenly — a medieval village that seems to have grown from the tuff rock on which it is built. Park outside the walls and walk inside. It’s one of those places you didn’t know existed and never forget.
Lunch in Pitigliano. Look for acquacotta — a humble vegetable soup that tells centuries of Maremma cooking.
Pitigliano → Saturnia (20 km)
Twenty kilometres and you’re at the hot springs of Saturnia — the free ones, the Cascate del Mulino. Not the springs with the hotel, but where the sulphurous water flows warm between the rocks and you sit in it without paying anything.
If you have time, take a dip. If you don’t feel like getting wet, sit down anyway and watch.
Saturnia → Siena (90 km)
The return is long but beautiful. Head back north through the inland Maremma — Manciano, Scansano, then the crete again and Siena.
There is nothing extraordinary about this stretch. It’s just road, hills, and the thought that the weekend is over but that somewhere, on one of these bends, you left something you didn’t know you were carrying.
Practical Notes
Where to sleep: San Quirico d’Orcia has several agriturismi at reasonable prices. Book in advance in high season.
Petrol: fill up in Siena before leaving and in Montalcino on the first day — petrol stations in the inland areas are rare.
What not to do: set the GPS to “fastest route”. Set it to “secondary roads” or, better still, set nothing at all and follow the signs for the villages.
The secret: don’t plan everything. Leave a couple of free hours each day. The best things on this route are not on the map.
“The road is in no hurry to end.” Especially in Tuscany.
