Best CyclingTrip

Tuscany, Italy

Gravel in the Chianti, from Greve in Chianti

Start point

Greve in Chianti

Distance

65 km

Elevation gain

1200 m D+

Duration

One day

Difficulty

Hard

Best season

April to June, September to October

Gravel

The Chianti, Tuscany’s best-known wine region, offers tougher gravel terrain than the neighbouring Crete Senesi: sharper hills, oak forest between rows of sangiovese vines, and a network of “strade bianche” connecting wine villages without following the same road for long.

A hilly route between vines and forest

From Greve in Chianti, the route climbs toward Panzano and then Radda in Chianti through scenery that alternates terraced vineyards with holm oak forest, on white gravel roads typical of the area. Expect around 65 km and 1,200 m of cumulative climbing for a full loop — noticeably tougher than the Crete Senesi route south of Siena, which stays generally smoother over a comparable distance.

Getting the ride right

A 40mm gravel tyre with some tread suits this terrain better than the Crete Senesi, since the forested sections can get loose underfoot. Wine villages punctuate the route at regular intervals, making supply stops easy — and tasting, as long as it’s saved for the end.

When to go

April to June or September to October, avoiding the hot, dry Tuscan summer that leaves the forested terrain dusty and the effort harder on an already hilly route.

Good to know

Greve in Chianti, considered the gateway to the wine region, has a choice of accommodation geared toward wine tourism, with convenient access to Florence and Siena for a trip combining cycling with sightseeing — and, for Tuscan gravel enthusiasts, a good complement to the Strade Bianche near Siena, under an hour’s drive away.

Getting to Greve in Chianti

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Where to stay near Greve in Chianti

A selection of well-located places to stay so you can start the ride fresh.

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Recommended gear

Frequently asked questions

How does the Chianti differ from the Strade Bianche near Siena?+

The terrain is hillier and more wooded: the Chianti alternates vine-covered slopes with oak forest, adding up to noticeably more climbing over a comparable distance. The Crete Senesi, south of Siena, offer a more open landscape and a generally smoother profile instead. The two complement each other well in the same Tuscan trip rather than overlapping.

Can you stop for wine tasting along the way?+

That's one of the route's draws: Greve in Chianti, Radda in Chianti and Panzano rank among the main Chianti Classico producing villages, with plenty of cellars open for visits. Better to save any serious tasting for the end of the ride.

Other nearby spots