The White Roads, Done Properly
This week takes us across the most iconic Strade Bianche sectors including Monte Sante Marie, Montalcino, Pienza and the Crete Senesi. We ride past cypress lined lanes, through wine estates with deep roots and into towns where gelato is practically a recovery tool. The week ends with the Nova Eroica, a festive and non competitive event that celebrates the beauty of gravel riding in Tuscany.
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Ride the classic Strade Bianche sectors with full support and relaxed pacing.
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Experience Tuscanyโs finest flavours from Brunello tastings to pecorino workshops.
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Finish with Nova Eroica a joyful sportive with gourmet feed stations and village festival energy.
Included in this trip:
We organise the logistics so you can enjoy every gravel sector, every view and every plate of fresh Tuscan food.
- 7 nights in boutique hotels and agriturismi in Siena, Pienza and Montalcino
- Daily breakfasts with fresh Italian produce
- Mid ride cafรฉ stops, picnic lunches and dinners with paired wines
- Nova Eroica entry with logistics and on site support
- Vineyard visit with Brunello di Montalcino tasting
- Cheese workshop in Pienza
- Fully guided rides with support vehicle and mechanic
- Luggage transfers between each location
- Airport or train station transfers from Florence or Pisa
- Travel to and from Italy
- Bike hire fee if renting
- Personal purchases, drinks outside meals and travel insurance
The White Roads, in Full Colour
Gravel, cypress and a well earned glass at dayโs end.
Planning & itinerary
5 - 12 April 2026
Across eight days we link Siena, Val dโOrcia, Pienza, Montalcino and Chianti on a gravel cycling tour shaped by culture, rolling landscapes and warm Tuscan hospitality. Expect white roads, good food and evenings spent with new friends.
Arrival, welcome & bike set-up.
25 km | 300 m+
We welcome you to Siena and settle into our boutique hotel before heading out for a gentle spin toward Monteriggioni. It is an easy introduction to the week and a great chance to enjoy the first taste of Tuscan gravel.
In the evening we gather on Piazza del Campo for our welcome dinner, a beautiful way to begin the week together.
70 km | 900 m+
We ride the southern gravel sectors toward Radi and Vico dโArbia. The roads are smooth, scenic and perfect for settling into a steady rhythm.
Lunch is relaxed and local before we return to Siena through quiet vineyard tracks.
80 km | 1,300 m+
Today brings one of Tuscanyโs most iconic gravel landscapes. The Crete Senesi offers rolling white clay hills and views that stretch in every direction.
We then tackle Monte Sante Marie, a famous Strade Bianche sector that rewards patient pacing. We finish in Buonconvento for dinner and a peaceful night.
65 km | 1,000 m+
We ride gravel terraces above San Quirico dโOrcia and descend toward Pienza, a Renaissance jewel known for its pecorino.
In the afternoon we join a cheese workshop and settle into a charming agriturismo for the evening.
75 km | 1,400 m+
We climb gently toward Montalcino and stop at a Brunello estate for a guided tasting. The scenery is classic Tuscany with vineyards, farmhouses and long gravel lanes.
The afternoon is free to explore the medieval town or join a second optional loop.
85 km | 1,500 m+
We cross toward Chianti on a mix of ridgelines and quiet sectors. The final descent brings us into Gaiole, the birthplace of the Eroica movement.
After settling in, we attend the rider briefing for Nova Eroica and enjoy a relaxed evening.
90 km option | 1,500 m+
Today we join the Nova Eroica, a joyful non competitive ride with festival energy, gourmet feed stations and spectacular scenery. Ride your pace, enjoy the atmosphere and celebrate at the finish.
We end the day with a shared dinner, a glass of Brunello and plenty of laughter.
Goodbyes & Departure.
We enjoy a final breakfast together before transfers to Florence or Pisa. Legs may be dusty but spirits are high and the white roads stay with you long after you leave.
Why Choose This Tour?
We ride every must see sector including Monte Sante Marie, Montalcino and the Crete Senesi with time to look around, take photos and enjoy the ride. No crowds, no pressure, just the beauty of Tuscany shared with a friendly group.
You will know where to find the best espresso in Asciano and why these roads are beloved around the world.
Brunello, pecorino and olive oil tastings are led by people who make them with passion. You meet the producers, hear their stories and enjoy flavours that reflect the region.
It creates a deeper connection and brings meaning to every meal, glass and tasting.
We keep groups small and rides well supported so you can enjoy the scenery and company without stress. Our hotels and agriturismi offer comfort and charm, perfect after a day on the white roads.
By the end of the week you will understand why Tuscany is a gravel paradise and why this tour sets the standard.
Talk to a Tuscany Gravel Expert
Have a question about this gravel cycling tour, or need help fine-tuning the details? Whether itโs finding the perfect espresso stop or advice on tyre pressure for the Strade Bianche, our team is here to help. Drop us a message, and weโll get back to you quicker than a Tuscan sunset disappears behind the hills!
Book a call
Click here to schedule a free personal consultation with one of our event planners.
