Florence to Siena Scenic Drive: The Chianti SR222 Route
By Gillian Boyd Published 14 August 2026
Skip the toll road. Discover our favourite scenic route, from Florence to Siena on the Chianti SR222, past vineyards, olive groves and 5 medieval hilltop towns.
The Via Chiantigiani SR222 goes through the picturesque hilltop towns of Greve in Chianti, Panzano in Chianti, Castellina in Chianti, Radda and Gaiole.
Although the fastest route (taking about an hour and a quarter) from Florence to Siena is the Raccordo Autostradale Firenze – Siena toll road, I strongly recommend taking the scenic Chianti SR222 route from Florence to Siena instead.
The SR222 Chianti route is only 69km long, is free and passes through the world famous Chianti wine region with its many vineyards, olive groves and pretty medieval hill top villages.
Starting in Florence, the Via Chiantigiani passes through Greve in Chianti, Panzano, Castellina, Radda, Gaiole and finally reaches Siena.
We spent the day travelling the route and stopped at 3 small towns along the way, each with its own character. In between we admired the picture postcard landscape, watching it change from lush green to gold as we travelled south.
Panzano hilltop town in Tuscany
Drive, Cycle or Walk – it’s your choice
Although we drove the Chianti SR222 in a hire car we had collected in Florence, the Via Chiantigiani (its full name) also offers other options.
There are a range of cycling routes along the Chianti Classico Cycle Network both on and off the road.
The Eroica race is on the first Sunday in October with vintage bicycles from Sienese Chianti to Crete Sensesi and the Val d’Orcia. The 209km route is open all year. It is considered heroic to complete Eroica because the bikes are vintage and so lack modern technology and gears. Many of the participants wear vintage or retro clothes like the vintage style merino wool bicycle top we noticed for sale at Castello di Brolio Vineyard. For more information see visittuscany.com
Or if you prefer a slower pace, there are walking trails including the 78km long ancient pilgrimage route known as the Via Romea Sanese. See Visitchianti.net
Piazza Matteotti at Greve in Chianti, Tuscany
Greve in Chianti
We passed through a few small towns before we stopped at Greve in Chianti. It had good shops selling local food and wine produce but also a couple with leather goods and clothes stores.
The centre of the town is dominated by the triangular shaped Piazza Matteotti surrounded by attractive restaurants and bars. It’s a pleasant place to potter around.
Black Rooster Logo
Wine from the Chianti region is easily recognisable from the black rooster logo and can be found in any Enoteca (wine shop). There is a small wine museum too and on Saturday mornings there is a market.
Parking
We spent a couple of Euros and parked at one of the many paid carparks in the town using a parking app. There was plenty of space. The town was very quiet.
Local Chianina Cattle
Over lunch we learned about the native cattle, the Chianina, the largest in the world and easily identifiable by its porcelain-white coat. It has been highly prized since Etruscan and Roman times and is traditionally used for Bistecca all Fiorentina, the famous Tuscan steak.
A few days later we would see the Chianina pull the cart displaying the Drappellone, a hand painted silk banner that is the prize for the world-famous horse race and historic festival, the Palio di Siena.
Black Rooster statue in Panzano
Panzano in Chianti
Just 10 minutes down the road was Panzano. We parked in a layby at the edge of town and walked up some cool leafy steps into the town. It was hot (it was June and Europe was having a heatwave) and we seemed to have coincided with siesta time as most of shops were closed. It was 3.30pm.
We went into the Church which always seems to be at the highest point, and then wandered around taking in the wide-open views of the vineyards and landscape that seem to spread for miles and miles.
The sky dotted with a few clouds to stop it from being boring. Even the new housing development on the edge of the town, was built to complement and blend.
Rooster Statue
Then to our surprise we came across a modern giant black rooster statue. Closer inspection revealed it was the mark for Chianti wine which can be found on all wine bottles from this region. ‘Chianti Classico since 1716’ was the inscription.
Castellina in Chianti, Tuscany.
Castellina in Chianti
Entering the town, we were pleasantly diverted by the Art Trail of sculptures by Alberto Inglesi dotted about the town and the shops as we made our way uphill to the main square.
Inhabited since the 7th century, Castellina in Chianti has been built to last. Looking more like a fort, perched at the top of the hill (isn’t it always), is the ancient Rocca di Castellina, housing the Archaeological Museum of Sienese Chianti.
Next to it was a square with two wine bars. Pretty flower pots added some colour and it just felt peaceful to sit there in the late afternoon, enjoying the gentle breeze and watching the world go by.
Radda and Gaiole
We passed through these pretty villages on our way to Siena but didn’t stop this time as we knew we would be back again soon.
Final Thoughts
Travel is not always about the destination, it’s the journey. If you have the time, it is worth driving the Via Chiantigiani, scenic route SR222 and stopping at medieval towns along the way. But if you are unable to spare the time to explore the hilltop towns, I can confirm the views are better on the SR222 Via Chiantigiani than the toll road, the Raccordo Autostradale Firenze.