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Routes
Road cycling routes
Italy
Tuscany
Arezzo
Cavriglia

Radda in Chianti – Castellina in Chianti loop from Cavriglia

Routes
Road cycling routes
Italy
Tuscany
Arezzo
Cavriglia

Radda in Chianti – Castellina in Chianti loop from Cavriglia

Hard

5.0

(4)

360

riders

Radda in Chianti – Castellina in Chianti loop from Cavriglia

05:27

107km

1,790m

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 26.7 km for 152 m

Waypoints

A

Start point

Parking

Get Directions

6.78 km

Valico di Montegrossi

Mountain Pass

2

15.2 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

3

18.8 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

26.5 km

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

5

26.7 km

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

6

29.2 km

Panoramic road between Castellina in Chianti and San Donato

Highlight (Segment) • Cycleway

From Castellina in Chianti, the SP101 heads north.
Directly behind the town sign comes the road leads beautifully on or right and left of the ridge. Little traffic and fantastic …

Translated by Google •

Tip by

7

56.5 km

Luiano Vineyard

Highlight • Structure

Along the road that from the bridge over the Greve (signs) goes up towards Mercatale in Val di Pesa, there is this beautiful winery in a panoramic position.

Translated by Google •

Tip by

8

79.1 km

Panzano in Chianti Village

Highlight • Settlement

Panzano in Chianti is like many villages on a hill and therefore offers a nice view.
For us racing cyclists, it also means the highest point of, in this case, …

Translated by Google •

Tip by

9

79.6 km

Black Rooster Sculpture, Panzano in Chianti

Highlight • Monument

nice place in Chianti with the great restaurant by Dario Checchini

Translated by Google •

Tip by

98.2 km

Passo di Coltibuono

Mountain Pass

B

107 km

End point

Parking

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Way Types & Surfaces

Way Types

53.8 km

52.4 km

494 m

< 100 m

Surfaces

104 km

3.15 km

< 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 (680 m)

Lowest point (120 m)

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Weather

Powered by Foreca

Saturday 8 August

36°C

22°C

0 %

Additional weather tips

Max wind speed: 5.0 km/h

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