Why this road
This is the road the region is named for. It curves gently over the hills, always a little higher than the valleys, so you look out over rows of vines and lines of cypresses. Greve has its arcaded piazza, Panzano its famous butcher, Castellina its medieval covered street, and you reach Siena the old way, from the hills to the north.
The route
- AFlorence
Leave Florence to the south-east towards Grassina. Watch out for the ZTL zones in the centre, they are camera-controlled.
- 1Greve in Chianti
The first big wine town, with a triangular piazza lined with arcades and wine shops. A good place for a coffee.
- 2Panzano in Chianti
A small hill village above a bowl of vineyards. The road runs just below the old centre.
- 3Castellina in Chianti
On a ridge between the Elsa and Pesa valleys. Walk the Via delle Volte, a medieval street covered by a vaulted passage.
- BSiena
The road comes down through Quercegrossa. Park outside the walls and walk up to the Piazza del Campo.
Stops worth it
Half an hour for the piazza, a wine shop and the view back over the valley.
The covered Via delle Volte and the Etruscan tomb mound just outside town. Many wineries nearby offer tastings, usually booked in advance.
Light and the best time
You drive south, so in the afternoon the sun is in front of you and to the right. Leave Florence around 3 pm and the last hour into Siena is in warm, low light, with the vineyards on your left lit from the side. In the morning the sun comes from the left and the hills to the west are front-lit, also lovely, just less golden.
April to June and September to October. The grape harvest is usually from mid-September to early October, a beautiful time with busy farm traffic. Summer is hot and hazy at midday. The road is open all year.
By vehicle
Exactly the right speed for the roof down: gentle curves, smells of rosemary and cypress, and a stop every few kilometres.
Smooth, flowing curves rather than hairpins. Plenty of side roads into the hills if you want more.
Easy all the way. Just remember: whoever drives does not taste.
Chianti is classic road cycling country, but hilly. The SR222 has traffic on weekends; quieter side roads run parallel through the vineyards.
Good to know
No toll, and the fast route via the Florence to Siena expressway is toll-free too. Florence and Siena both have restricted traffic zones (ZTL) in the old town with cameras and fines, so park outside the centre. Italy has strict drink-driving limits, book a tasting where you can walk or bring a driver who does not drink.
Route checked against OpenStreetMap on 2 November 2026. Roads, closures and rules change: always check before you go and follow local signs.
Questions
How long is the Chiantigiana from Florence to Siena?
About 1 h 30 of driving without stops, roughly 20 minutes more than the expressway. With stops in Greve and Castellina, plan a half day or more.
What is the SR222 Chiantigiana?
The old road from Florence to Siena through the Chianti Classico wine region, via Greve, Panzano and Castellina.
Can I drive into Siena's old town?
No, the historic centre is a restricted traffic zone. Use one of the car parks outside the walls and walk or take the escalators up.
Is the Chiantigiana busy?
On summer weekends, yes, around Greve especially. Weekdays and spring or autumn are much calmer.