| Style | Luxury Cycling Experience · Guided by a Professional |
| Duration | 6–11 May 2026 · 24–29 Jun 2026 · 16–21 Sep 2026 · 5–10 Oct 2026 |
| Suggested Start/Finish | Florence → Val d'Orcia, Tuscany · Italy (flexible upon request) |
| Riding Level | Intermediate · Regular road cycling experience recommended |
| Best Season | May · June · September · October |
| Essence | Ride Tuscany's most legendary roads alongside a former Tour de France stage winner — a cycling experience unlike anything else in Italy |
This private journey is entirely bespoke, tailored to your pace, passions, and preferences.
From €6,450 per person – Also available as a private experience. Let us craft your perfect cycling experience.
Tuscany is one of the most iconic cycling destinations in the world. White gravel roads cutting through clay hills, cypress-lined lanes dropping into UNESCO valleys, vineyards that have been producing wine since before cycling existed. Riders come from every corner of the world to experience cycling in Tuscany — and most of them leave wishing they had gone deeper.
This luxury Tuscany cycling tour goes deeper.
Built around Daniele Bennati — former professional cyclist, Grand Tour stage winner and one of the most respected names in Italian cycling — this experience gives you something no standard Tuscany bike tour can offer: the roads seen through the eyes of someone who has raced them at the very highest level. Bennati won stages at the Tour de France, the Vuelta a España and the Giro d'Italia. He knows every climb, every descent, every hidden road in this landscape. For six days, that knowledge is entirely yours.
The journey takes you through the finest cycling terrain in southern Tuscany. You will ride the legendary Strade Bianche gravel roads of the Crete Senesi — the white roads that have defined a generation of professional racing. You will climb Monte Amiata through forests and mountain landscapes that most visitors to Tuscany never see. You will follow the wine roads of Montalcino and lose yourself in the rolling beauty of Val d'Orcia, one of the most photographed landscapes on earth and one of the finest places in the world to ride a bike.
Every evening, you return to the ADLER Spa Resort Bagno Vignoni — one of Tuscany's most exclusive wellness retreats, set in the heart of Val d'Orcia. Panoramic thermal pools, spa treatments, exceptional cuisine and elegant accommodation create the perfect environment to recover, reflect and prepare for the next day on the road.
The journey also includes a private cellar visit and Brunello tasting at Ciacci Piccolomini d'Aragona, one of Montalcino's most celebrated historic estates — a moment that belongs as much to this landscape as the riding itself.
This is the Tuscany cycling experience for those who want more than a beautiful route. It is sport, culture, gastronomy and the unique perspective of a former professional cyclist woven into six days of riding in one of Italy's most celebrated regions.
Available on selected dates — or as a fully private experience for your group.
Why ride Tuscany with Daniele Bennati
- Insider knowledge of Tuscany's most iconic roads — including the legendary Strade Bianche, shared by a rider who has raced them at the professional level
- Race insight from the professional peloton — pacing strategies, terrain reading and cycling intelligence gained across a career at the very highest level
- Access to hidden Tuscan routes far from the typical tourist roads, selected personally by Bennati
- A complete cycling journey blending sport, culture and gastronomy across one of Italy's most celebrated landscapes
