There’s a particular ritual to a cycling morning here: gloves pulled on at the terrace table, cleats clicked into place against the same stone wall that’s stood since long before anyone clipped into a pedal, one last look at the valley before the wheels start turning. Then the gate, the gravel, and the hills take over.
This coming weekend, that ritual multiplies by several thousand. L’Eroica, the vintage cycling gathering that has defined Gaiole in Chianti every October since 1997, returns on 3-4 October 2026 – and it’s as good a reason as any to talk about why this stretch of Chianti isn’t just beautiful to look at from a terrace. It’s genuinely built for riding.
A weekend for steel frames and wool jerseys
L’Eroica isn’t a race. It’s closer to a pilgrimage for people who believe cycling’s soul lives in down-tube shifters, toe clips, and pre-1987 steel – the “beauty of fatigue,” as founder Giancarlo Brocci put it when he started the event to help preserve the region’s disappearing white gravel roads.
Five routes fan out from Gaiole this year, from a manageable 46 km loop through the Valle del Chianti past Brolio Castle, to the full 209 km L’Eroica – nearly 3,900 metres of climbing, with some riders not reaching the finish until after 10pm. Whichever distance you ride (or simply watch), the villages fill with vintage bicycles, period wool, and the low hum of a few thousand people who all agree that gravel roads are worth defending.
The riding doesn’t end when the peloton goes home
What L’Eroica really does is put a spotlight on something locals and returning guests already know: this particular fold of Chianti, around Gaiole, is quietly one of the best places in Tuscany to actually ride a bike – any weekend of the year, on any kind of bike.
We took out a Komoot tracker on a recent loop straight from Podere L’Aquila’s own gate: 70.5 km, 1,414 metres of elevation gain, a fastest point of 46 km/h on the descents. The route climbs out through the property’s own olive groves, drops onto the strade bianche – the white gravel roads L’Eroica exists to protect – threads through working vineyards, and returns via forest tracks shaded by pine and oak. No traffic to speak of. Just the sound of tyres on gravel and, occasionally, a church bell from a hill town in the distance.
That’s the real case for this part of Chianti: it isn’t one showcase route built for an event. It’s a whole network of strade bianche, quiet asphalt, and forest single-track that locals have been riding for training long before L’Eroica made it famous – Brolio Castle, the Chianti Classico vineyards, the rolling Crete Senesi further south, and Siena itself within striking distance for a longer day out.
Riding from Podere L’Aquila
A few things make the property itself a good base, whether you’re here for L’Eroica weekend or any other:
You start climbing (and finish descending) from the door. No transfer to a trailhead – the gravel begins where the terrace ends.
Bike-friendly by habit, not just by amenity list. Guests park bikes against the stone walls, hose down gear on the lower terrace, and there’s always somewhere shaded to leave a bike overnight.
Routes for every mood. Road riders can chase Chianti Classico’s rolling vineyard climbs; gravel and mountain bikers have the forest tracks and white roads that made the region famous; and for a gentler day, a flat loop through the valley floor is never far away.
A view that makes the climbing worth it. However hard the last ascent felt, it tends to end at a point where Siena’s skyline is visible across the valley – a fairly good argument for one more hill.
If you’re coming for L’Eroica weekend
The event runs Saturday and Sunday, 3-4 October 2026. If you’re planning to watch, ride, or simply soak up the atmosphere in Gaiole, the full property – both pools, the restaurant, all eleven apartments – is open and running exactly as usual through 11 October, so there’s no need to plan around any seasonal changes for this particular weekend.
From 12 October 2026, once L’Eroica has wrapped and the vintage bicycles have gone home, Podere L’Aquila settles into its quieter autumn rhythm: two apartments, Alloro and Pino, remain open with the upper pool, and meals move to the upper house’s own dining room. The riding, if anything, gets even better once the roads empty out again.
Worth knowing before you pack the bike
Bring your own bike if you can – box or bike-bag transport is straightforward via Florence or Pisa airports, both within reach.
Wide tyres (32mm or more) are worth it if you plan to explore the strade bianche rather than stick to asphalt.
Layer up for October mornings – valley mist tends to burn off by mid-morning, but the descents are cold before it does.
Chianti doesn’t need an event to justify a ride through it. L’Eroica just happens to be the weekend when everyone else notices what’s been here all along.
Planning a cycling stay around L’Eroica or any other weekend? Check dates and rates directly on our site, or message us on WhatsApp – we’re happy to point you toward the right route for the day.
