Tuscany Road Trip: Florence to the Val d'Orcia (4 Days)
Drive through Tuscany from Florence to the Val d'Orcia — Chianti vineyards, Siena, cypress-lined hills and wine towns, day-by-day route, where to sleep and real costs.
Rough estimate — fuel + nights at typical rates. Get an exact figure in the calculator.
The route on video
This unhurried drive through Tuscany links Renaissance Florence with the cypress-lined hills of the Val d’Orcia, a UNESCO-listed landscape of golden fields, hilltop towns and world-class wine. You drive on the right. It is a short route made for lingering over food and views — and a warning: most historic centres are ZTL limited-traffic zones watched by cameras, so park outside the walls and walk in.
Day 1 — Florence to Siena (75 km)
Leave Florence and wind south through the Chianti vineyards, stopping to taste as you go, to the medieval city of Siena and its shell-shaped Piazza del Campo.
Day 2 — Siena to the Val d’Orcia (50 km)
Drop into the Val d’Orcia for its picture-book views around San Quirico d’Orcia and Pienza, the “ideal Renaissance town” and home of pecorino cheese.
Day 3 — Montepulciano and Montalcino (40 km)
The great wine towns of Montepulciano (Vino Nobile) and Montalcino (Brunello). Taste responsibly and always keep a designated driver.
Day 4 — Back to Florence (110 km)
Return north, perhaps via the famous towers of San Gimignano, and drop the car in Florence.
Costs
Use the cost calculator to price fuel and nights for your exact dates. Watch for ZTL camera fines in town centres — park outside and walk. Budget fuel, agriturismo farm stays and plenty of wine; book agriturismi early in summer.
Where to stay on this route
Pick your dates and see what is available in Montepulciano.
See places to stay — Montepulciano →Affiliate link — we may earn a commission at no extra cost to you.
🚦 Know before you go
Tolls. No vignette; the A1 autostrada south to the Valdichiana/Chiusi exit charges a per-km toll (approx €7–9) via ticket-and-barrier paid by cash/card or Telepass, while the scenic SR2 Via Cassia through the valley is toll-free.
Good to know. Hilltop towns like Pienza, Montalcino and Montepulciano have ZTL centres, so park outside the walls and walk in to avoid camera fines that rental firms pass on with a fee.
Estimate your exact costs in the cost calculator. Prices are approximate — check official sites before you travel. Some links are affiliate links.
Plan this trip
Where to sleep
Hotels & B&Bs → Holiday homes & apartments → Campsites (bookable) → Campervan & overnight spots →Tours & tickets
Find things to do →Affiliate link — we may earn a commission at no extra cost to you.
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