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Castellina In Chianti

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

Castellina In Chianti

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

Hard

5.0

(2)

109

riders

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

03:42

77.6km

1,080m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: April 20, 2026

Tips

Temporary access restrictions

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

After 76.8 km for 277 m

Waypoints

Start point

Parking

Get Directions

2.29 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

11.0 km

Start of L'Eroica in Gaiole in Chianti

Highlight • Cycleway

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

Tip by

11.0 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

21.5 km

Gaiole in Chianti

Highlight • Settlement

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

Translated by Google •

Tip by

62.5 km

Monteriggioni Castle

Highlight • Castle

Sections of via francigena between Siena and Monteriggioni. Climb and descend sweet and challenging in one of the most beautiful contexts in Tuscany

Translated by Google •

Tip by

76.2 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

76.9 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

77.2 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

77.6 km

End point

Parking

Way Types & Surfaces

Way Types

54.2 km

19.2 km

1.88 km

1.80 km

318 m

198 m

< 100 m

Surfaces

76.7 km

576 m

166 m

161 m

< 100 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (610 m)

Lowest point (180 m)

Weather

Sunday 31 May

27°C

15°C

75 %

Additional weather tips

Max wind speed: 7.0 km/h

to get more detailed weather forecasts along your route

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

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

SR429: Castellina in Chianti to Radda in Chianti

Start of L'Eroica in Gaiole in Chianti

Radda in Chianti

Gaiole in Chianti

Monteriggioni Castle

Rocca of Castellina in Chianti

Castellina in Chianti

Black Rooster Statue, Castellina in Chianti

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