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

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

Hard

5.0

(5)

173

riders

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

04:02

77.8km

1,410m

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

Waypoints

Start point

Train Station

Get Directions

10.7 km

Gelateria di Castellina

Highlight • Cafe

The best gelato in Chianti. Try it and tell us we are wrong...

Tip by

11.6 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

40.8 km

Gaiole in Chianti

Highlight • Settlement

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

Translated by Google •

Tip by

48.2 km

Passo di Coltibuono

Mountain Pass

50.6 km

View of the Road to Badia a Coltibuono

Highlight • Viewpoint

50.6 km

View of Castello di San Donato in Perano

Highlight • Viewpoint

If you turn right towards the castle you travel along a stretch of dirt road towards Gaiole.

Translated by Google •

Tip by

54.9 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

58.6 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

67.1 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

77.8 km

End point

Train Station

Way Types & Surfaces

Way Types

40.2 km

36.5 km

834 m

303 m

Surfaces

77.5 km

303 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 (180 m)

Weather

Today

Sunday 23 August

34°C

17°C

0 %

Additional weather tips

Max wind speed: 9.0 km/h

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

Gelateria di Castellina

Black Rooster Statue, Castellina in Chianti

Gaiole in Chianti

View of the Road to Badia a Coltibuono

View of Castello di San Donato in Perano

Radda in Chianti

SR429: Castellina in Chianti to Radda in Chianti

Rocca of Castellina in Chianti

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