La Leonessa Gravel: Tuscany's Coolest Summer Ride (2026)
By nine in the morning in July, the classic strade bianche loops around Gaiole already sit in full sun. La Leonessa gravel is the route locals use instead. It climbs out of the Sieve valley near Pontassieve, then disappears into the shaded forest roads of Vallombrosa before the day turns properly hot. First-time riders often expect another dusty Chianti loop. Instead, they find long stretches of beech and silver fir cover. On top of that, a permanent gravel network sits open every day of the year. Finally, a village swimming hole waits at the bottom of the descent. In short, this guide covers the route itself, the forest roads through Vallombrosa, Secchieta, and Pratomagno, plus the pools at Loro Ciuffenna that make the whole loop work as a genuine summer escape.
Most visitors planning a Tuscany gravel trip head straight for the routes made famous by L'Eroica. That instinct makes sense on paper. However, it overlooks a quieter, cooler alternative that local riders have used since 2015. This one is built specifically around terrain that stays comfortable when Chianti does not.
What Is La Leonessa Gravel?
La Leonessa began as a vintage cycling event near Pelago. The Pro Loco of Pelago organises it, with backing from the municipalities of Pelago, Rufina, and Reggello. The first edition rode out in April 2015. It traced old rural paths through the Chianti Rufina and the Montagna Fiorentina, many of which had fallen out of use. Along the way, riders pass the Frescobaldi family's Nipozzano estate and stop at Ferrano for a rest. Eventually, the route climbs the legendary unpaved ascent toward Passo della Consuma.
Alongside the historic ride, a dedicated La Leonessa gravel variant now exists under the same name. It offers a short loop of roughly 33 kilometres and a longer one of about 61 kilometres, with close to 1,500 metres of climbing. Both use modern gravel bikes rather than the pre-1987 steel-framed machines required for the vintage event. Either way, the destination stays the same: the cool, forested climb into Vallombrosa.
Ride the La Leonessa Gravel Route Any Day of the Year
Since 2018, La Leonessa's long route has existed as a permanently signposted trail, funded in part by the Comune di Pelago. As a result, the full 80-kilometre course, marked with trailside signage the whole way, is rideable 365 days a year. It is not limited to the official event weekend. For a visiting cyclist, this detail matters more than it might first appear. There is no need to plan a trip around one single spring date, or fight for a start slot. Instead, you can load a GPS track and go whenever the weather, and your legs, are ready.
Official details on the ciclostorica and the permanent route sit with the Comune di Pelago, the event's municipal patron. Wikiloc also hosts a GPS track of the permanent route for anyone who wants to follow it turn by turn.
Why La Leonessa Gravel Beats L'Eroica in the Heat
L'Eroica, the famous vintage ride through Gaiole in Chianti, returns for its 2026 edition on October 3 and 4. That date is no accident. Chianti's classic strade bianche sit at relatively low elevation, fully exposed to the sun. Consequently, organisers moved the main event to autumn, precisely because high summer makes those roads punishing. In other words, even L'Eroica's own calendar admits that Chianti in August is not the moment for its route.
La Leonessa gravel solves that same problem differently. Rather than waiting for cooler weather, its route gains elevation and ducks under tree cover through Vallombrosa's centuries-old forest. As a result, you can ride real Tuscan gravel through the hottest stretch of summer, with no need to book an autumn trip instead. This is the core reason La Leonessa deserves more attention than it gets. It is the true hidden gem for gravel biking in Tuscany, solving the same heat problem that shaped L'Eroica's own calendar.
Through Vallombrosa, Secchieta, and the Pratomagno Ridge
Vallombrosa sits at roughly 1,000 metres of elevation. It lies inside a biogenetic nature reserve, established in 1977 and centred on an abbey founded back in 1036. The wider reserve spans from about 470 metres near the hamlet of Tosi up to around 1,440 metres at Monte Secchieta. So temperatures drop noticeably as the road climbs. Beech and silver fir dominate the canopy here. Even on a hot July afternoon, that shade alone makes a real difference.
Monte Secchieta, at 1,449 metres, is one of the highest points on the Pratomagno ridge. It also marks the boundary between the provinces of Florence and Arezzo. Also, a small refuge with a bar sits near the summit, handy for a coffee stop before the descent. For gravel riding specifically, stick to the main ridge road rather than the narrower mountain-bike single track that branches off it. The ridge road is the section built for wider gravel tyres. Visit Tuscany covers the wider Pratomagno and Valdarno area in more depth for anyone planning a longer countryside stay.
Cool Off at Loro Ciuffenna's Pozze
The route's natural finish line, at least for a summer ride, is the village of Loro Ciuffenna. It is officially listed among Italy's most beautiful villages. Its stone bridge and narrow lanes still follow their medieval layout today. Indeed, the village mill, built around 1100 and still active, is thought to be the oldest working water mill in Tuscany. It grinds chestnuts into the flour used in local baking.
A few minutes' walk from the main square, the Massette area offers a gentle, shallow stretch of the Ciuffenna stream. It is good for cooling off without much effort. Further upstream, about a fifteen-minute walk away, sits the Pozzone, the village's best-known natural pool. There, a deep basin carved from pale stone sits beneath a small waterfall, popular for weekend swims and jumps.
Neither spot counts as a managed bathing area. There are no lifeguards, no marked paths, and no safety equipment on site. So caution genuinely matters here. Wear proper footwear on the rocks, check the current before getting in, and skip it entirely after heavy rain, when the stream runs faster and murkier than usual.
Skip the Crowded Circuit: Ride La Leonessa Gravel Right
Over 8,000 riders from more than 50 countries took part in L'Eroica last year. Accordingly, Gaiole's narrow lanes fill up fast on event weekend. By contrast, La Leonessa gravel's permanent route sees a fraction of that traffic on an ordinary summer Tuesday. That said, if you would rather not navigate unmarked forest junctions alone, a guided option is often the smarter call. This is particularly true on a route mixing narrow forest roads with genuine elevation gain.
Our own sustainable hiking and gravel-biking experiences are built around exactly this kind of terrain. Indeed, small groups, real countryside, and a pace with nothing to do with a coach schedule define them. That is a different experience from an impersonal group tour treating a forest climb like a checklist item. Instead, a private, locally-led ride through this same landscape lets you actually stop at the refuge on Secchieta, or take an extra ten minutes at the Pozzone, rather than sticking to someone else's timetable.
Practical Tips for Riding La Leonessa Gravel in Summer Heat
A few adjustments make a real difference on a summer ride through this terrain.
- Start at dawn if possible; the climb out of Pontassieve is the most exposed section before the forest cover begins
- Carry more water than usual, since refreshment points from event weekend are not staffed on a normal riding day
- Run wider gravel tyres, ideally 40mm or more, for comfort on the forest gravel and the descent into Loro Ciuffenna
- Check mobile signal expectations before you go, since coverage inside the forest sections is patchy
- Pack sun protection even though the route stays shaded for long stretches, because the climbs to and from Pelago sit in open country
Frequently Asked Questions
What is La Leonessa gravel?
La Leonessa gravel is a modern gravel-bike route based on the historic La Leonessa ciclostorica near Pelago, Tuscany. It runs through the Chianti Rufina hills and into the forests of Vallombrosa, with a short option of about 33 kilometres and a long one of roughly 61 kilometres.
Is La Leonessa gravel harder than L'Eroica?
The long La Leonessa gravel route climbs about 1,500 metres over 61 kilometres, which is demanding but shorter than L'Eroica's 209-kilometre main route. Overall difficulty depends on which distance you choose for each event, so the two are not directly comparable on effort alone.
Can I ride La Leonessa gravel outside the event weekend?
Yes. Since 2018, the long route has existed as a permanently signposted trail, rideable any day of the year. Therefore, you do not need to wait for the spring ciclostorica dates to ride it.
Is it safe to swim at Loro Ciuffenna's pozze?
The Massette and Pozzone swimming spots are natural, unsupervised areas with no lifeguards or facilities. So wear sturdy footwear, check the current first, and avoid swimming after heavy rain, when water levels and speed both rise.
How far is Loro Ciuffenna from Florence?
Loro Ciuffenna sits roughly 55 kilometres from Florence, about an hour's drive through the Valdarno. It also works well as the finish point of a longer La Leonessa gravel day out from the city.
Do I need a special bike for La Leonessa gravel?
The modern gravel variant welcomes standard gravel bikes with wider tyres. Only the separate vintage ciclostorica event requires a steel-framed road bike built before 1987.
Want to ride La Leonessa gravel with a local guide instead of a solo GPS file? Our sustainable gravel-biking and hiking experiences cover this same Vallombrosa and Pratomagno terrain in small, private groups. Browse the full range of tours on our homepage, or explore our Florence urban hikes for a lower-key outdoor day in the city itself. Planning a stop in Florence before or after the ride? Our Florence Off the Beaten Path: From Real Locals map has our own picks for where to eat and drink. Get in touch through our contact form or at info@outoftheboxflorence.com to plan your route.
