Castellina in Chianti – Rocca of Castellina in Chianti loop from Castellina in Chianti

Castellina In Chianti

Castellina in Chianti – Rocca of Castellina in Chianti loop from Castellina in Chianti

Moderate

5.0

(6)

205

riders

Castellina in Chianti – Rocca of Castellina in Chianti loop from Castellina in Chianti

02:07

42.4km

690m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: September 24, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions. Check ahead to confirm restricted segments are open to the public.

After 577 m for 304 m

Waypoints

Start point

Parking

Get Directions

414 m

Black Rooster Statue, Castellina in Chianti

Highlight • Monument

Castellina in Chianti is located in the province of Siena, in the Chianti Classico area. He is easily accessible from the Elsa Valley, Arbiatal and Pesatal. Due to the altitude, …

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653 m

Castellina in Chianti

Highlight • Settlement

Castellina in Chianti is located in the province of Siena, in the Chianti Classico area. Accessible from several valleys, it offers breathtaking views. It is a crucial point for cyclists …

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1.33 km

Rocca of Castellina in Chianti

Highlight • Castle

Castellina in Chianti stands on a chain of hills in the Chianti area. The heart of the town is the ancient fortress, designed in the second half of the fifteenth …

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1.38 km

Gelateria di Castellina

Highlight • Cafe

The best gelato in Chianti. Try it and tell us we are wrong...

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3.36 km

Panoramic View from the Chiantigiana

Highlight • Viewpoint

Panoramic view of Siena and Montemaggio

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29.3 km

Descent from Badesse

Highlight • Trail

The descent from Badesse is a famous hilly stretch on the Via Francigena and part of the Grande Anello di Siena. Characterized by a steep slope that starts from the …

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30.1 km

Lonano–San Leonino Scenic Road

Highlight (Segment) • Cycleway

Beautiful road, good tarmac, prepare to go up and down and repeat. Sometimes around 13% but never very long.

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34.3 km

San Leonino Water Fountain

Highlight • Rest Area

I don't know where this cinnamon is in San Leonino...

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42.4 km

End point

Parking

Way Types & Surfaces

Way Types

27.9 km

12.3 km

1.66 km

539 m

Surfaces

42.2 km

196 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (570 m)

Lowest point (220 m)

Weather

Sunday 11 October

22°C

11°C

41 %

Additional weather tips

Max wind speed: 15.0 km/h

to get more detailed weather forecasts along your route

Comments

April 6, 2025,Giro in bici da corsa second part Radda-Castellina in Chianti-Siena (cont)

From Radda the road decends then climbs gradually into Castellina in Chianti and from there on its all pretty much downhill from there through Quercegrossa and back to Siena. From this BASIC loop there are many optional route throughout.