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Routes
Road cycling routes
Italy
Tuscany
Siena
Monteriggioni

Castellina in Chianti – Radda in Chianti loop from Castellina in Chianti-Monteriggioni

Routes
Road cycling routes
Italy
Tuscany
Siena
Monteriggioni

Castellina in Chianti – Radda in Chianti loop from Castellina in Chianti-Monteriggioni

Hard

147

riders

Castellina in Chianti – Radda in Chianti loop from Castellina in Chianti-Monteriggioni

04:55

95.8km

1,660m

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: July 31, 2026

Tips

Includes a segment in which cycling is not permitted

After 3.34 km for 78 m

Waypoints

A

Start point

Train Station

Get Directions

3.38 km

Rocca di Staggia

Castle

2

13.1 km

Scenic Road from Poggibonsi to Castellina in Chianti

Highlight (Segment) • Trail

If you are looking for a scenic, low-traffic and relaxed road up to Castellina in Chianti you will find it here.
On the approximately 18 kilometers with 450 meters of altitude, the slope remains exceptionally even and never rises above 4, a maximum of just 5%.
A pleasure trip ...

Translated by Google •

Tip by

3

31.4 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 traveling around Chianti. From Elsatal there are four roads that lead up there. At the main intersection there is a fountain and bars nearby.

Translated by Google •

Tip by

4

31.7 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, the place also offers great views into these valleys.
For us racing cyclists it is an important traffic junction for tours in the Chianti area or for round trips in it.
Four roads lead up from the Elsa Valley alone.
There is a fountain at the main intersection and some bars around it.

Translated by Google •

Tip by

5

34.3 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

6

50.6 km

Lecchi in Chianti

Highlight • Settlement

A beautiful Chianti village.

Tip by

66.3 km

Passo di Coltibuono

Mountain Pass

8

68.6 km

View of the Road to Badia a Coltibuono

Highlight • Viewpoint

9

73.0 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

10

85.2 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 century by Giuliano da Sangallo. Via Ferruccio, the Church of San Salvatore, some patrician palaces and some places where you can taste a good glass of Chianti Classico make it a perfect resting place.

Translated by Google •

Tip by

B

95.8 km

End point

Train Station

Loading

Way Types & Surfaces

Way Types

63.3 km

28.0 km

3.01 km

1.34 km

260 m

Surfaces

95.4 km

210 m

146 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 (680 m)

Lowest point (100 m)

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Weather

Powered by Foreca

Today

Sunday 23 August

34°C

17°C

0 %

Additional weather tips

Max wind speed: 9.0 km/h

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