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Road cycling routes

Gaiole In Chianti

Radda in Chianti – Gaiole in Chianti loop from Montegrossi

Road cycling routes

Gaiole In Chianti

Radda in Chianti – Gaiole in Chianti loop from Montegrossi

Moderate

4.7

(18)

225

riders

Radda in Chianti – Gaiole in Chianti loop from Montegrossi

01:51

33.6km

680m

Road cycling

Moderate road ride. 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: October 9, 2026

Waypoints

A

Start point

Parking

2.28 km

Passo di Coltibuono

Mountain Pass

2

4.66 km

View of the Road to Badia a Coltibuono

Highlight • Viewpoint

3

4.69 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

4

9.00 km

Radda in Chianti Historic Center

Highlight • Historical Site

Radda in Chianti with its walls is worth a visit

Translated by Google •

Tip by

5

9.14 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

6

9.16 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

7

18.5 km

Lecchi in Chianti

Highlight • Settlement

A beautiful Chianti village.

Tip by

8

27.1 km

Gaiole in Chianti

Highlight • Settlement

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

Translated by Google •

Tip by

9

27.4 km

Start of L'Eroica Gaiole in Chianti

Highlight • Cycleway

pretty here, very pretty

Showing Translation

Tip by

B

33.6 km

End point

Parking

Way Types & Surfaces

Way Types

21.7 km

10.5 km

1.47 km

Surfaces

32.2 km

1.44 km

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Elevation

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

Highest point (680 m)

Lowest point (290 m)

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Weather

Powered by Foreca

Today

Wednesday 14 October

24°C

11°C

0 %

Additional weather tips

Max wind speed: 9.0 km/h

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