Gaiole in Chianti
The small historic centre of Gaiole, like Greve, emerged in the late Middle Ages as a market town serving the nearby castles.
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L’Eroica is one of those events that is difficult to explain to those who have not experienced it. Born in 1997 in Gaiole in Chianti, when 92 seekers of feeling and emotion set off on the first edition, challenging the dust of Tuscan white roads on vintage bicycles and dressed in a rainbow of wool jerseys, the event has grown into a global phenomenon without losing any of its original spirit. Every year, on the first weekend of October, the hills of the Chianti region around Siena transform into a timeless stage, where thousands of cyclists from around the world mount bicycles built before 1987, wearing wool jerseys and leather shorts, carrying tubular tyres across their shoulders just as champions did in another era.
L’Eroica is not a race in the conventional sense: the rankings count for little or nothing. What matters instead is the substance, that spirit of adventure which returns cycling to its most authentic roots — dust, mud, exhaustion, conviviality — when sport captivated all of Italy, divided between the camps of Coppi and Bartali. The white roads of Chianti and the Crete Senesi provide its natural stage, a symbol of human-scale transport and a landscape that has remained extraordinarily intact. It is no coincidence that in the 2025 edition there were 8,328 actual participants, with over 40% coming from abroad: a figure that tells the international dimension of an event born in a hamlet of just a few hundred inhabitants better than any other statistic.
Those who arrive at Gaiole in Chianti for L’Eroica do not find simply a sporting event: they find an experience that blends cycling, culture, gastronomy and landscape in an unrepeatable formula. The refreshment stops along the route are tables laden with ribollita, Tuscan bread, cured meats, cheeses and Chianti — not merely energy refuels but moments of pause and sharing. The vintage market, side events, exhibitions and concerts transform the weekend into a festival spread throughout the village that involves the entire hamlet and visitors who choose to watch rather than pedal.
The idea arose from a desire to save the white roads of Chianti — at risk of being paved over — transforming them into a heritage to be protected and valued through cycling. Conceived by Giancarlo Brocci and promoted by the Parco Ciclistico del Chianti Association, the event presented itself from the outset as a celebration of the beauty of effort and the taste of enterprise: words that still today define the DNA of the event. Pre-war cycling — that of the pioneers who tackled hundreds of kilometres on heavy bicycles, without technical assistance, with wheels sinking into mud — returned to the light of day with all its genuine epic character.
The regulations are precise: bicycles must be built by 1987, with steel frames, external lever gearshift, no onboard computers or plastic parts. Clothing must respect period style: wool jersey, leather or wool shorts, shoes with rigid soles. Before each start, bicycles and clothing are inspected — an inspection that is itself part of the spectacle. Authenticity is not a decorative detail: it is the substance of the event.
From that 1997 edition, L’Eroica has pursued an unstoppable path. After Eroica Cuba in 2024 and NOVA Eroica Istria in 2025, 2026 will see a new historic milestone: the first edition of Eroica China, likely in the Hong Kong region. A dream born in the heart of Chianti that has become a global movement capable of connecting places and people in the name of the bicycle and beauty.
L’Eroica takes place over two days and offers five routes for as many levels of fitness and ambition, all traced over the white and paved roads of the Siena Chianti region, Valdarbia, Crete Senesi and Val d’Orcia. Road signage, created in collaboration with the Province of Siena, guides cyclists along the entire route with directional signs and kilometre markers. Roads are open to normal vehicular traffic: respecting the Road Code is an obligation for every participant.
This is the original route, the most demanding with over 3,700 metres of elevation gain: an epic adventure for those who want to experience L’Eroica in all its essence. The ride lasts at least 15 hours; the last riders return to Gaiole in Chianti sometimes after 10 pm. It takes place on Saturday, with departures from early morning. With 110 kilometres of gravel, it crosses deepest Chianti, Val d’Arbia and the Crete Senesi in a succession of landscapes that justify every kilometre of effort. In the 2025 edition, 1,644 cyclists chose this route, almost a fifth of the total.
The middle route for those who don’t want to miss out on the challenge but seek a balance between distance and landscape. It passes through spectacular scenery amongst the Sienese hills and includes around 70 kilometres of gravel. It also takes place on Saturday, with morning departures. It was the most popular route in the 2025 edition, with 2,078 participants representing 25% of the total: a figure that tells how powerfully the name “Crete Senesi” appeals even to those who are not cycling extremists.
The first of three Sunday routes, it balances difficulty and scenic beauty and is ideal for those who want to tackle an intense experience without facing an extreme test. With around 35 kilometres of gravel, it descends into the Arbia valley between villages and churches of great charm.
Perfect for those seeking a balance between effort and pleasure, cycling among vineyards and medieval villages. The Gallo Nero symbol — emblem of Chianti Classico — gives its name to a route that crosses the heart of Chianti’s wine region, with around 35 kilometres of white roads among vineyards and olive groves. Sunday morning is also the best time to witness the spectacle of departures: the village of Gaiole comes alive with coloured jerseys, gleaming bicycles and the warmth of a community that experiences L’Eroica as a collective celebration.
The gateway to the L’Eroica experience for those approaching for the first time or preferring to enjoy the landscape with contained physical effort. It takes around three hours and offers beautiful views. Teenagers aged 13 to 17 can also take part in this route, with parental permission: a detail that reveals the inclusive and family-friendly nature of the event.
Registration opens several months in advance on the official website eroica.cc and sells out quickly: it is essential to monitor opening dates and register promptly. Those without a vintage bicycle can hire one locally thanks to the Ciclofficina Eroica, operating in Gaiole in Chianti from the Thursday before the event: bikes are supplied already checked and compliant with regulations.
Gaiole in Chianti is located in the heart of Chianti Classico, around 30 km from Siena and 60 km from Florence. During the L’Eroica weekend, accommodation throughout the area fills up months in advance: booking at least six months ahead is a necessity, not just advice. The village of Gaiole offers some properties within a few steps of the starting point, whilst nearby you will find farm stays, villa rentals and charming hotels nestled among the vineyards of Chianti Classico, many of which offer services dedicated to cyclists such as supervised bike storage, laundry facilities and energy-boosting menus.
Those who choose to turn L’Eroica into a longer stay can combine the event with a visit to the local wineries, a tour of medieval villages such as Radda in Chianti and Castellina in Chianti, or an excursion as far as Siena and San Gimignano.
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