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Routes
Road cycling routes
Italy
Tuscany
Siena
Gaiole In Chianti

Gaiole in Chianti – Radda in Chianti loop from Gaiole in Chianti

Routes
Road cycling routes
Italy
Tuscany
Siena
Gaiole In Chianti

Gaiole in Chianti – Radda in Chianti loop from Gaiole in Chianti

Hard

5.0

(3)

151

riders

Gaiole in Chianti – Radda in Chianti loop from Gaiole in Chianti

04:43

97.7km

1,380m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: November 4, 2026

Tips

Temporary access restrictions

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

After 22.2 km for 152 m

Waypoints

A

Start point

Bus stop

Get Directions
1

370 m

Gaiole in Chianti

Highlight • Settlement

Gaiole in Chianti, a characteristic Sienese village surrounded by famous vines

Translated by Google •

Tip by

2

10.7 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

14.3 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

22.0 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

22.3 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

24.7 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

52.1 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

74.7 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

75.1 km

Vecchio lavatoio

Archaeological Site

B

97.7 km

End point

Bus stop

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Way Types & Surfaces

Way Types

62.9 km

34.5 km

369 m

< 100 m

Surfaces

96.3 km

1.52 km

< 100 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 (620 m)

Lowest point (120 m)

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Weather

Powered by Foreca

Wednesday 4 November

16°C

3°C

0 %

Additional weather tips

Max wind speed: 9.0 km/h

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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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