Gravel Riding Around San Gimignano: Il Casolare as Your Perfect Base

Few places in Italy marry cycling and landscape as effortlessly as the hills around San Gimignano. The strade bianche — those iconic white gravel roads — wind through vineyards, olive groves, and medieval hilltop villages, offering a riding experience you simply won't find anywhere else. This is Tuscany at its most raw and most beautiful, best explored from the saddle.

Il Casolare Le Terre Rosse sits right at the heart of it all. More than a place to sleep, it's a fully equipped cycling base — the kind of setup that means you can roll out of the door every morning and lose yourself in the countryside, without a logistical worry in the world.

The hotel is part of a true Gravel Bike Region: routes start directly from the property and fan out across some of the most scenic mixed-terrain riding in the country. And through the partnership with Roadbike, certified local guides are on hand to take you out on rides tailored to your ability — from gentle rolling panoramics to more technical gravel challenges for those who want to push harder.

Head out from the hotel towards Colle di Val d'Elsa, tracing the Sentiero Elsa river path through forest, where clear turquoise pools catch the light between the trees. The route continues to Casole d'Elsa — a satisfying mix of quiet tarmac and unhurried country lanes — before looping back through wide open hillside panoramas. You'll be back in time for a proper late-afternoon wind-down before dinner. 

46.3 km / 760 m elevation 
From the hotel, the road takes you through Ulignano and on to Poggibonsi, where the imposing Fortezza di Poggio Imperiale rises above the town — a striking piece of military architecture that stops you in your tracks. Push on to Colle di Val d'Elsa and climb up to Colle Alta, the ancient medieval quarter perched above the modern town. It's the perfect place for a coffee stop with a view. Back at the hotel in time for a swim before dinner. 

40.1 km / 780 m elevation 
This ride takes you to Certaldo Alto, a perfectly preserved medieval hilltop village and the hometown of Giovanni Boccaccio, author of The Decameron. 

The approach through geometrically patterned vines and olive terraces is worth the ride alone. Wander the brick-paved lanes at the top, then return to the hotel via some of the most scenic back roads in the area — a fitting end to the day. 

Our country hotel is set up specifically for cyclists. On-site bike rental covers road bikes, mountain bikes, hybrids and e-bikes; secure, workshop-equipped bike storage takes care of your own machine. For anything more technical, a network of partner shops and mechanics is nearby.

All routes are available as digital files, ready to load onto your device before you leave. A self-service laundry keeps your kit fresh. Post-ride recovery is taken seriously: tailored nutrition menus and sports massage are both available on-site.

Coming back to Il Casolare after a long day in the saddle is part of the experience. Cool down in the pool, then settle into aperitivo hour at the Bruschetta Cafè in the garden, with the Tuscan hills going golden in the evening light.

Dinner at the Hostaria Le Terre Rosse is the kind of meal that earns itself: handmade pasta, wood-grilled meats, and a glass of local wine that somehow tastes like the landscape you've just ridden through. There's no rush to finish.

Then the real quiet of the Tuscan countryside — no traffic, no city noise — settles in. Sleep deeply. Wake up ready to do it all again