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Italy
Tuscany
Siena
Castellina In Chianti

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

Routes
Road cycling routes
Italy
Tuscany
Siena
Castellina In Chianti

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

Moderate

5.0

(6)

199

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: June 26, 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

A

Start point

Parking

Get Directions

1

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, …

Translated by Google •

Tip by

2

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 …

Translated by Google •

Tip by

3

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 …

Translated by Google •

Tip by

4

1.38 km

Gelateria di Castellina

Highlight • Cafe

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

Tip by

5

3.36 km

Panoramic view of Siena and Montemaggio

Translated by Google •

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6

29.3 km

Descent from Badesse

Highlight • Trail

7

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.

Tip by

8

34.3 km

San Leonino Water Fountain

Highlight • Rest Area

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

Translated by Google •

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B

42.4 km

End point

Parking

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Way Types & Surfaces

Way Types

28.0 km

12.3 km

1.59 km

539 m

Surfaces

42.2 km

196 m

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Elevation

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)

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Weather

Powered by Foreca

Monday 13 July

35°C

19°C

-- %

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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.
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