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)

111

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: July 19, 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

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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.

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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.

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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”.

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21.5 km

Gaiole in Chianti

Highlight • Settlement

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

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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

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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 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.

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

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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, 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.

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Tip by

77.6 km

End point

Parking

Way Types & Surfaces

Way Types