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L'Eroica di Gaiole in Chianti – permanent route

Giacomo Tuscany_Bike_Guide

L'Eroica di Gaiole in Chianti – permanent route

Bike Touring Collection by Nicola Amadini



8-9 h

/ day

128 mi

11,500 ft

11,475 ft

L'Eroica di Gaiole in Chianti is Italy's leading vintage cycling event. It was born in 1997 thanks to the passion of Giancarlo Brocci, journalist, writer and organiser of sporting events. Every year in October, it welcomes over 7,500 participants.

In this Collection, I present the permanent route, which covers a total of 209 kilometres (130 mi) in the heart of Tuscany. Riding through Chianti, the Crete Senesi and the wonderful Val d'Orcia, an extraordinary heritage is revealed. You'll ride along little-travelled roads, with challenging climbs and descents, twists and turns and landscapes steeped in history and with a strong sense of identity.

The technical characteristics of the route are ideal for cycle touring, alternating tarmac roads and dirt tracks, with a total elevation gain that is neither too low nor too high (around 3,800 metres / 12,500 ft).

The landscape is marvellous: olive groves and vineyards, rows of cypress trees, rolling countryside, stone farmhouses, and breathtaking viewpoints. In Crete Senesi, you’ll find art, culture, spirituality, spas and excellent food – in short, a slice of Tuscan paradise that deserves to be discovered and appreciated.

The Collection is divided into two Tours, showcasing the essence and purpose of l'Eroica . With each pedal stroke, you’ll uncover the authenticity of the roots of cycling as a popular sport, rediscovering the beauty of hard work and the taste of enterprise.

The first Tour leads from Gaiole in Chianti to Torrenieri, while the second takes you back to the starting point, closing the loop. Gaiole is easily reached by car (about 30 minutes from Siena) and has several car parks. There are also numerous accommodation facilities in the area, which I recommend reserving in advance, especially in summer and at weekends.

The route can be completed with any type of bicycle and throughout the year. The hills look different in every season.

On The Map


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L'Eroica di Gaiole in Chianti – full route

128 mi

11,500 ft

11,500 ft

Last updated: November 21, 2023

Plan your own version of this adventure in the multi-day planner based on the stages suggested in this Collection.

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  1. Map data © OpenStreetMap contributors

    Stage 1: Gaiole in Chianti to Torrenieri – L'Eroica

    61.5 mi
    7.6 mph
    5,425 ft
    5,750 ft
    Expert gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

    The track proposed for the first day has a total length of about a hundred kilometers and winds through wonderful hills in a pleasant up and down.


    The departure is from the center of Gaiole in Chianti, a small village with a long agricultural tradition and a charming historic centre. Leave its quaint

    translated byView Original


  2. 09:47
    66.0 mi
    6.7 mph
    6,075 ft
    5,725 ft
    Expert gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

    The second Stage of this Collection foresees the departure from the center of Torrenieri, a hamlet of Montalcino, in the direction of the cemetery.


    The road is mainly unpaved and characterized by continuous ups and downs.


    It runs alongside the Castello di Tosona area and at the crossroads follow the signs

    translated byView Original



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Collection Stats

  • Tours
  • Distance
    128 mi
  • Duration
    17:55 h
  • Elevation
    11,500 ft11,475 ft

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