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Italy
Tuscany
Siena
Monteriggioni

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

Routes
Road cycling routes
Italy
Tuscany
Siena
Monteriggioni

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

Moderate

4.7

(7)

89

riders

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

02:28

49.1km

790m

Road cycling

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

Last updated: May 19, 2026

Tips

Includes segments that go up or down a series of steps

You may need to carry your bike.

After 23 m for 46 m

After 49.1 km for 46 m

Waypoints

A

Start point

Train Station

Get Directions

1

1.54 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

2

13.2 km

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

15.8 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

24.4 km

Eroica is the annual non-competitive cycling event that takes place in Chianti and starts at this specific highlight spot.

Tip by

5

24.5 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

6

36.8 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

7

43.7 km

San Leonino Village View

Highlight • Viewpoint

Small village of houses lost in an extremely panoramic point of Chianti between Castellina in Chianti and Badesse (near Siena).

Translated by Google •

Tip by

8

48.4 km

Descent from Badesse

Highlight • Trail

B

49.1 km

End point

Train Station

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Way Types & Surfaces

Way Types

35.7 km

12.9 km

374 m

< 100 m

< 100 m

Surfaces

49.0 km

< 100 m

< 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.

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Weather

Powered by Foreca

Wednesday 3 June

28°C

14°C

0 %

Additional weather tips

Max wind speed: 14.0 km/h

to get more detailed weather forecasts along your route

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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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