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Routes
Road cycling routes
Italy
Tuscany
Siena
Castellina In Chianti

Castellina in Chianti – Radda in Chianti loop from Castellina in Chianti

Routes
Road cycling routes
Italy
Tuscany
Siena
Castellina In Chianti

Castellina in Chianti – Radda in Chianti loop from Castellina in Chianti

Hard

5.0

(2)

83

riders

Castellina in Chianti – Radda in Chianti loop from Castellina in Chianti

04:04

76.2km

1,480m

Road cycling

Hard road ride. Very 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: July 31, 2026

Tips

Temporary access restrictions

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

After 331 m for 277 m

Waypoints

A

Start point

Parking

Get Directions

1

532 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

2

852 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

3

3.45 km

SR429: Castellina in Chianti to Radda in Chianti

Highlight (Segment) • Cycleway

This pretty road (SR429), between Castellina in Chianti and Radda in Chianti, is always winding and winding at about 600 meters above sea level. It is a delightful ride with always very beautiful views of the surrounding valleys and hills.

Translated by Google •

Tip by

4

12.1 km

Radda in Chianti

Highlight • Settlement

A walk through the narrow, winding streets and numerous ornate vaulted passages transports you back to bygone medieval times, as if Radda were still the capital of the “Lega del Chianti”.

Translated by Google •

Tip by

5

24.7 km

Rocca di Castagnoli

Highlight • Settlement

pretty here, very pretty

Showing Translation

Tip by

6

25.2 km

View on Castagnoli

Highlight • Viewpoint

From this point you have an overview of Castagnoli, a small medieval village in the municipality of Gaiole in Chianti, surrounded by woods, olive trees and rows of cypresses. In …

Translated by Google •

Tip by

7

25.8 km

Monteluco Climb

Highlight (Segment) • Climb

Moderate slope with very little traffic - but the more shade.

Translated by Google •

Tip by

31.3 km

Passo di Monte Luco

Mountain Pass

9

56.7 km

Lecchi in Chianti

Highlight • Settlement

A beautiful Chianti village.

Tip by

B

76.2 km

End point

Parking

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Way Types & Surfaces

Way Types

48.2 km

27.6 km

214 m

178 m

128 m

Surfaces

75.9 km

214 m

128 m

< 100 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 (770 m)

Lowest point (290 m)

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Weather

Powered by Foreca

Monday 10 August

36°C

22°C

17 %

Additional weather tips

Max wind speed: 12.0 km/h

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