The standard Tuscany road trip follows a well-worn path: Florence to Siena via the Chiantigiana, then south through the Val d'Orcia to Montalcino and Montepulciano. It is a magnificent route. It is also driven by approximately 400,000 people each year, many of them in rented Fiats approaching the bends at speeds that would concern a rally driver.
A Different Route
We suggest beginning in Volterra, the ancient Etruscan city perched 550 metres above the Cecina valley. It is less visited than San Gimignano, better preserved, and surrounded by extraordinary landscapes — the pale clay badlands of the Balze to the west, the olive groves and cypress-lined lanes to the south.
From Volterra, follow the minor road southeast toward Massa Marittima, a fortified hill town of extraordinary completeness that most visitors to Tuscany have never heard of. The Piazza Garibaldi, with its Romanesque cathedral, is among the finest medieval squares in Italy.
The Maremma
South of Massa Marittima lies the Maremma — the wild coastal strip of Tuscany that was marshy and malarial until the nineteenth century. It remains less developed than inland Tuscany and considerably less visited. The Parco Regionale della Maremma offers walking and cycling through coastal scrub, with herds of the long-horned Maremmana cattle and, in spring and autumn, excellent birdwatching.
The small towns of Pitigliano and Sorano, built into and over volcanic tufa cliffs, are genuinely remarkable. Pitigliano in particular — its buildings rising directly from the rock — is one of the most dramatically sited towns in Italy and receives perhaps a tenth of the visitors of its more famous neighbours.
Practical Notes for Driving
Tuscany's secondary roads — the white gravel strade bianche — are navigable in a standard hire car provided you drive slowly and sensibly. A 4WD is not necessary unless you plan to venture onto farm tracks. GPS is unreliable on minor roads; download offline maps before you leave and carry a paper Touring Club Italiano map of Tuscany as backup.
Timing: May and September are ideal. July and August bring heat, traffic and higher prices. The vendemmia (grape harvest) in September fills the air with extraordinary smells and the towns with a purposeful energy that is quite different from summer tourism.
Fuel: Fill up in larger towns. Rural petrol stations are sparse and not always open when you need them.
Where to Stay
An agriturismo — a working farm offering accommodation — is the ideal base for this route. Standards vary enormously: at the best, you eat the farm's own olive oil and wine, sleep in converted stone buildings of considerable charm, and wake to views unchanged since the Renaissance. Look for properties with genuine agricultural activity rather than those that are farms in name only.
Booking directly with the agriturismo, rather than through platforms, almost always results in better rooms and more genuine hospitality.
The Route Summary
- Day 1–2: Volterra — the Etruscan museum, the Balze, the alabaster workshops
- Day 3: Massa Marittima — the cathedral, the mining museum, lunch in the piazza
- Day 4–5: Maremma — the Parco Regionale, Pitigliano, Sorano
- Day 6: Drive north through the Val d'Orcia to Montalcino for Brunello
- Day 7: Montepulciano and the return to Florence or Siena