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This is not Chianti. There are no vineyards here, no cypress-lined drives leading to a farmhouse. What you find instead is something stranger and more beautiful: vast, treeless clay hills that shift from pale gold to burnt sienna depending on the light, eroded into ridges and gullies over centuries, stretching in silence to every horizon.
The locals call it the lunar landscape of Tuscany. Once you ride through it, you understand why.
This tour takes you through the heart of the Crete Senesi on e-bike, along the Via Lauretana, one of the most dramatic panoramic roads in all of Italy, before ending the day exactly as this landscape deserves: immersed in the natural thermal waters of Rapolano Terme.
This is not a day trip. It is a full sensory experience — wide open sky, ancient roads, and water that has been flowing through the rock since before anyone thought to name this place.
Both options depart at 9:00 am from Asciano and return to the same point around 1:00 pm for lunch, before transferring together to Rapolano Terme for the spa. The route and the highlights change, the lunch and the thermal waters don’t.
Asciano is a small medieval town sitting quietly at the edge of the clay hills, the kind of place that has barely changed in the last five hundred years. The tour begins here, and almost immediately the landscape opens up.
From the first kilometers, you are inside the Crete. The road climbs and falls through terrain that feels almost prehistoric: no trees, no fences, just the slow rhythm of the hills and the wide arc of the sky above.
The backbone of both routes is the Via Lauretana, a centuries-old pilgrimage road that once connected the Via Francigena to the Sanctuary of the Santa Casa di Loreto. For generations, merchants, pilgrims, and artists travelled this road. Today, very few cyclists know it exists.
The panoramic views from the Via Lauretana are among the finest in all of Tuscany. The clay hills roll out in every direction, unmarked and uninterrupted, only the landscape, the sky, and the steady hum of the e-bike beneath you.
Both routes follow segments of the Eroica, the legendary gravel race celebrating the roads and traditions of this region since 1997. You are not racing. But you are riding the same roads.
| OPTION 1 — Easy | 30 km | 600 m elevation | Paved roadsThe iconic Tuscany, up close The shorter route, all on paved roads, perfect for any fitness level. |
At one point along the route, a view opens up that you will have seen before, in paintings, in films, in photographs, without ever knowing exactly where it was.
The hill in front of Baccoleno, with its sinuous cypress-lined drive winding up through golden fields, is one of the most iconic images in all of Tuscany. In the Crete Senesi, between soft curves and perfect light, this view captures the most photographed and dreamed-of soul of the Tuscan landscape. Seeing it from the saddle is something different entirely.
Founded in 1313 by Bernardo Tolomei in the remote “desert of Accona” among the Crete Senesi, the Abbazia di Monte Oliveto Maggiore is one of the most fascinating monastic complexes in Tuscany.
The tradition holds that this isolated place was chosen for silence, prayer, and contemplation. The heart of the visit is the magnificent Grande Cloister, decorated with 35 frescoes by Luca Signorelli and Il Sodoma depicting the life of Saint Benedict. The abbey church, the wooden choir, the refectory, and the surrounding landscape of cypresses and eroded clay hills complete a place that feels entirely outside of ordinary time.
| OPTION 2 — Moderate | 45 km | 850 m elevation | 50% gravel The wilder route More distance, more terrain — for those who want to go deeper into the Crete. |
At one point along the route, the road leads to an unexpected encounter: a stone sculpture set into the landscape, visible from a distance, belonging to the hills as if it has always been there.
The Site Transitoire was conceived in 1993 by French artist Jean-Paul Philippe. It is built from stone and open to the sky — a seat, a window, a threshold. On the summer solstice, the window concentrates the last light of the day into a single point. Philippe describes it as the outline of a house made of light and space, with no walls and no roof except the sky.
It is not a detour. It is one of the moments of the day.
Both tours return to Asciano around 1:00 pm. A light lunch of 100% organic local specialties is waiting, unhurried, generous, the right way to close the ride and prepare for what follows.
Ten minutes from Asciano, the natural thermal waters of Rapolano Terme have been flowing through the rock for centuries. The water is warm, mineral-rich, and restorative in the way that only truly natural things are.
After the ride, this is not indulgence. It is the logical conclusion of the day.
The Terme San Giovanni offers access to the thermal pools and park for the remainder of the afternoon, changing rooms, showers, and open-air pools where time passes differently. Optional extras (robe, towel, slippers kit and massages) are available on site.
Anyone who wants to see Tuscany at its most unexpected, off the main routes, under a wide sky, without a schedule.
| Duration | Hours | Distance | Elevation | Level | |
| Option 1 | Full day | 9:00 am – ~5:00 pm | 30 km (18.6 mi) | 600 m (1970 ft) | Easy |
| Option 2 | Full day | 9:00 am – ~5:00 pm | 45 km (28 mi) | 850 m (2790 ft) | Moderate |
Option 1 is the right choice for most guests: it’s shorter, fully on paved roads, and accessible to all fitness levels. Option 2 is for those who want a longer ride with more varied terrain, about half of it on gravel roads. Both options include the same lunch and the same spa afternoon.
For Option 1, no experience is needed at all, the e-bike handles the climbs effortlessly. For Option 2, some comfort on a bike is helpful given the gravel terrain and longer distance. In both cases the pace is relaxed and the guide adjusts to the group. We’ve had guests of all ages complete both options comfortably.
Yes, a professional guide accompanies the group for the full day. The bike ride ends around 1:00 pm in Asciano for lunch, then the group transfers together to Terme San Giovanni in Rapolano Terme. The afternoon at the spa is unstructured, you stay as long as you like.
Comfortable layered clothing for the ride, we provide the helmet. For the spa, bring a swimsuit and sunscreen. If you book the spa kit add-on (robe, towel, slippers), you won’t need to bring anything extra. Please let us know about any dietary requirements at booking, the Asciano lunch is fully adaptable.
Yes. Asciano is approximately 1 hour from Florence and 30 minutes from Siena. Transfer is available as an optional add-on, let us know at the time of booking.
Not included: personal travel insurance, additional beverages, personal expenses, spa treatments beyond standard pool access.
Optional extras (bookable at the time of reservation): transfer from Florence or Siena; spa kit (robe, towel, slippers); massage at Terme San Giovanni.
Remember to bring: swimsuit, sunglasses, sunscreen.
| Start / End | Asciano (same point) |
| Departure | 9:00 am |
| Bike ride ends | ~1:00 pm |
| Lunch in Asciano | ~1:00 – 2:00 pm |
| Transfer to Rapolano Terme | ~10 min by car |
| SPA — Terme San Giovanni | Afternoon — open end |
| Total distance | 30 km / 18.6 mi |
| Elevation gain | 600 m / 1970 ft — fully supported by e-bike |
| Experience level | No cycling experience required |
| Who it’s for | Couples, groups, families — all ages |
| Transfer from Florence / Siena | Available on request |
| Start / End | Asciano (same point) |
| Departure | 9:00 am |
| Bike ride ends | ~1:00 pm |
| Lunch in Asciano | ~1:00 – 2:00 pm |
| Transfer to Rapolano Terme | ~10 min by car |
| SPA — Terme San Giovanni | Afternoon — open end |
| Total distance | 45 km / 28 mi |
| Elevation gain | 850 m / 2790 ft — 50% gravel roads |
| Experience level | Some cycling experience recommended |
| Who it’s for | Couples, groups, families — all ages |
| Transfer from Florence / Siena | Available on request |
We create the perfect conditions for your UNFORGETTABLE holiday in Tuscany. Each tour is a mixture of 5 essences: adventure, art & history, nature, wellness, and food.
Our goal is to exceed your expectations. Respect for the environment, health & safety, quality and compliance with legal requirements are our main values.
© Tuscany Quintessence SRL
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P.IVA Num. 06863080484
Share Capital f.p. 15.000 euro
Company registered in Firenze – 661889
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