Photo: Luca Micheli / Unsplash
About This Route
The SR222 Chiantigiana connects the outskirts of Florence with Siena through Greve, Panzano and Castellina in Chianti. It is a focused 70 km ride of ridgelines, woodland, vineyards and working villages rather than the inflated all-Tuscany loop often described online.
Route plan
- Bagno a Ripoli to GrassinaStart southeast of central Florence to avoid the historic centre and its ZTL. The road leaves suburban traffic behind at Grassina and begins to follow the Chianti hills.
- Grassina to Greve in ChiantiStay on the SR222 through Strada in Chianti. The road alternates open ridges and shaded bends, with side roads and village entrances interrupting the flow.
- Greve to CastellinaClimb through Panzano toward Castellina. This is the most consistently curving part of the route, with worthwhile stops in the towns rather than on narrow verges.
- Castellina to SienaContinue via Fonterutoli and Querciagrossa toward Siena. Finish outside Siena's ZTL and walk or use local transport for the historic centre.
What the road is really like
The Chiantigiana is a flowing country road rather than a technical mountain route. Bends are frequent but moderate, and the attraction is the changing landscape and villages. Agricultural vehicles, cyclists and local traffic make aggressive overtaking a poor trade-off.
Shade can leave damp patches after rain, while driveways and junctions appear with little warning. The road is paved and beginner-friendly at a touring pace, but it is not empty: approach Greve, Panzano, Castellina and Siena expecting queues and pedestrians.
Planning the day
Visit Tuscany's official motorcycle itinerary measures 70 km and lists a full day because the route is meant to include stops. Three hours is a sensible moving-time estimate; allow six or more if you plan lunch and village visits.
Do not combine riding with wine tasting. Park outside historic centres, verify hotel access in advance and assume camera-controlled ZTL rules apply in Florence and Siena unless signs explicitly permit your motorcycle.
Fuel, food and stops
Reliable fuel options along or near the route include Greve in Chianti, Castellina. Top up before any long climb — pumps in mountain villages can be closed at lunch or on Sundays.
For food and coffee, Panzano, Radda in Chianti are solid stops. Aim for a proper sit-down lunch rather than a vending-machine snack — the locals eat well in this region.
⚠️ Safety and hazards to watch for
Specific hazards on this route include: Tourist traffic; Wine estate tours.
- Rural traffic
- Slow agricultural vehicles
- July–August brings scorching heat and heavy tourist traffic on narrow roads, and town centres (Florence, Siena) have ZTL limited-traffic zones — check current conditions.
Who this route suits
Tuscany Chiantigiana Road works especially well for photographers and slow-tour riders chasing scenery, adventure bike riders who don't mind the occasional rough patch. Recommended bike types are Touring, Adventure, but realistically anything in good mechanical condition with decent tyres will do the job — the road matters more than the badge on the tank.
Insider tips
- Visit San Gimignano towers
- Stop at wine estates
- Avoid the Palio crowds in Siena