Florence to Montepulciano: 4-Day Val d'Orcia Road Trip
Florence to Montepulciano in 4 days: 275 km through Chianti, Siena and the Val d'Orcia, with a day-by-day route, parking outside ZTL zones and where to sleep.
Rough estimate — fuel + nights at typical rates. Get an exact figure in the calculator.
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.
This trip is also in the free Roadcut trip planner: change the number of days and where you sleep each night, pick your vehicle to see the fuel cost, check the weather on the road, and open each day in Google Maps, Apple Maps or Waze.
Where to stay on this route
Night by night, in the towns this itinerary sleeps in.
- Night 1Hotels in Siena →
- Night 2Hotels in Pienza →Hotels in San Quirico d'Orcia →
- Night 3Hotels in Montepulciano →Hotels in Montalcino →
The search opens with sample dates a month from today — change them to yours on Booking. Affiliate link — we may earn a commission at no extra cost to you.
The route on video
Get this itinerary by email
The days and the nights in your inbox, with a link back here when you are ready to book.
We use your address only to send this itinerary, unless you tick the box. Privacy
⚡ By electric car on this route
54 charging stations within 1.5 km of the road.
For most of them OpenStreetMap does not record the power, so we cannot say where the fast chargers are — check your charging app before you set off.
According to OpenStreetMap and operators’ websites. Fast = a DC plug or 50 kW and more; not every station has its power filled in, so there may be more. See them on the planner map → · EV charging →
🚦 Know before you go
Tolls · Good to know
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.
Seen on the road
Travellers who drove these roads and filmed them.
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.
More roads nearby
New road trips in your inbox
One email when we publish a new European route — the full guide, map and real costs. No spam, unsubscribe anytime.