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

Start point

Train Station

Get Directions

3.38 km

Rocca di Staggia

Castle

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 …

Translated by Google •

Tip by

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 …

Translated by Google •

Tip by

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, …

Translated by Google •

Tip by

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

50.6 km

Lecchi in Chianti

Highlight • Settlement

A beautiful Chianti village.

Tip by

66.3 km

Passo di Coltibuono

Mountain Pass

68.6 km

View of the Road to Badia a Coltibuono

Highlight • Viewpoint

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

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 …

Translated by Google •

Tip by

95.8 km

End point

Train Station

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

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)

Weather

Monday 24 August

31°C

19°C

73 %

Additional weather tips

Max wind speed: 15.0 km/h

to get more detailed weather forecasts along your route

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

Scenic Road from Poggibonsi to Castellina in Chianti

Castellina in Chianti

Black Rooster Statue, Castellina in Chianti

SR429: Castellina in Chianti to Radda in Chianti

Lecchi in Chianti

View of the Road to Badia a Coltibuono

Radda in Chianti

Rocca of Castellina in Chianti

Nearby routes

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