Bike Tour Evolution
Luxury Tuscany Cycling Tour

Luxury Tuscany Cycling Tour by Daniele Bennati

Explore collectionExplore collection
Back to all toursBack to all tours
Details
Style Luxury Cycling Experience
Duration 6–11 May 2026 | 24–29 Jun 2026 | 16–21 Sep 2026 | 5–10 Oct 2026
Suggested Start/Finish Florence → Tuscany (flexible upon request)
Riding Level Intermediate – Suitable for cyclists with regular road experience
Best Season May | Jun | Sep | Oct
Essence Luxury Tuscany cycling tour with former professional cyclist Daniele Bennati. Ride the legendary Strade Bianche roads, explore Val d’Orcia landscapes and experience authentic cycling in Tuscany with Bike Tour Evolution.
Exclusively yours
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.
Design your ExperienceDesign your Experience

The Journey

 

Tuscany is one of the most iconic cycling destinations in the world. Rolling vineyards, white gravel roads and historic hilltop villages create the perfect landscape for an unforgettable Tuscany cycling tour.

This luxury Tuscany cycling tour with former professional cyclist Daniele Bennati offers riders the opportunity to experience the legendary Strade Bianche roads, the breathtaking landscapes of Val d’Orcia and the authentic rhythm of cycling in Tuscany.

Led by Daniele Bennati, former professional cyclist and elite sprinter with multiple Grand Tour stage victories, this experience combines the thrill of riding Tuscany’s most scenic roads with the elegance and comfort of a carefully curated luxury journey.

Over six days, riders will discover the hills of Val d’Orcia, the iconic Strade Bianche gravel roads of the Crete Senesi and the vineyards of Montalcino. Each route has been designed to combine scenic riding, authentic culture and memorable cycling moments across one of Italy’s most celebrated landscapes.

The program blends riding with carefully curated experiences: private wine tastings, cultural visits in historic Tuscan villages and moments to slow down and enjoy the atmosphere of the region. One of the highlights of the journey is a private visit to the historic estate of Ciacci Piccolomini d’Aragona, where guests enjoy an exclusive cellar tour and tasting.

Accommodation is at the ADLER Spa Resort Bagno Vignoni, one of Tuscany’s most refined wellness retreats. Surrounded by the landscapes of Val d’Orcia, the resort offers panoramic pools, spa treatments and gourmet cuisine — the perfect balance between performance, recovery and relaxation.

This is more than a bike tour in Tuscany. It is a cycling journey that blends sport, culture, gastronomy and the unique perspective of a former professional cyclist, creating an experience designed for riders who want to discover Tuscany beyond the ride.

 

Why Ride Tuscany with Daniele Bennati

 This experience is designed around the perspective of Daniele Bennati, former professional cyclist and Grand Tour stage winner who has spent years racing on the roads of Tuscany and beyond.

  • Insider knowledge of Tuscany’s most iconic roads, including the legendary Strade Bianche
  • Race insight from the professional peloton, sharing pacing strategies, terrain reading and cycling intelligence
  • Access to hidden Tuscan routes far from the typical tourist roads
  • A curated cycling experience blending sport, culture and gastronomy
Your Experience

Tuscany Cycling Tour Itinerary

Day 1 — Arrival in Val d’Orcia & Welcome Ride
Guests arrive in Tuscany and check in at the elegant ADLER Spa Resort Bagno Vignoni, nestled in the heart of the UNESCO-listed Val d’Orcia. After meeting the Bike Tour Evolution team and Daniele Bennati, enjoy a relaxed welcome ride through the surrounding countryside. Quiet Tuscan roads and rolling hills offer the perfect introduction to the landscapes that will define the week.

Day 2 — The Rolling Roads of Val d’Orcia
Today’s ride explores the breathtaking scenery of Val d’Orcia, one of the most iconic cycling regions in Italy. Gentle climbs, panoramic descents and historic hilltop villages create a rhythm that makes cycling in Tuscany so unique. Riders experience the essence of the Tuscan countryside: vineyards, cypress-lined roads and endless horizons.

Day 3 — Strade Bianche Experience
Ride the legendary Strade Bianche gravel roads that have made Tuscany famous in the world of professional cycling. Guided by Daniele Bennati, riders experience the iconic white roads of the Crete Senesi, a landscape of rolling clay hills and dramatic scenery. This is one of the most distinctive cycling terrains in the world.

Day 4 — Monte Amiata Challenge
A day dedicated to riders who love a true climbing challenge. The ascent of Monte Amiata offers a spectacular ride through forests and mountain landscapes rarely experienced by visitors to Tuscany. The climb rewards effort with sweeping views across the Tuscan countryside.

Day 5 — Montalcino & Tuscan Wine Roads
The final full riding day explores the beautiful roads surrounding Montalcino, home of the renowned Brunello wine. Flowing climbs and scenic ridgelines offer one last immersion in Tuscany’s landscapes. The day concludes with a special experience at Ciacci Piccolomini d’Aragona, where guests enjoy a private cellar visit and wine tasting.

Day 6 — Departure or Optional Morning Ride
After breakfast, guests may enjoy an optional short ride through the quiet roads around Bagno Vignoni before departure. A final moment to savor the atmosphere of Tuscany before concluding the journey.

Accommodation & Logistics

Guests stay at the refined ADLER Spa Resort Bagno Vignoni, one of Tuscany’s most exclusive wellness retreats located in the heart of Val d’Orcia. The resort combines elegant accommodation, panoramic thermal pools, spa treatments and exceptional cuisine — creating the perfect balance between performance and recovery.

Each ride is fully supported with professional guides, mechanical assistance and a dedicated support vehicle. Routes have been carefully designed by Bike Tour Evolution and Daniele Bennati to highlight Tuscany’s most beautiful cycling landscapes.

The journey blends sport, culture and gastronomy with exclusive experiences such as private wine tastings, visits to historic Tuscan villages and the special experience at Ciacci Piccolomini d’Aragona. This is more than a cycling tour — it is a curated exploration of Tuscany on two wheels.

Experience
Elevate your Biking
Experience
extra services

Optional Services & Tailor-Made Experiences

Captured moments
Gallery