Cycling Tuscany: Val d'Orcia white roads

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Bike Tours, E-bike tours


8 days





The beauty of this package is in the freedom it offers: without a guide, you are free to decide the timing, pace, and stops of your journey. Travel freely, travel your way!

3/5 Medium

Moderate, between 35 and 85 kilometers per day with an elevation gain between 300 and 1000 meters.



The starting point is the same as the ending point, with overnight stays in different hotels and daily stages.


Day 1: Arrival in Buonconvento
The enchanting medieval town of Buonconvento is rich in history and architecture and is completely surrounded by walls dating back to 14th century. Upon arrival, a transfer will take you to the Agriturismo where you will spend the next four nights. A delicious Tuscan dinner awaits for you!

Day 2: Buonconvento to Murlo and La Befa round tour (33 km, +584m -675m)
You will start riding in the rich countryside of Val d’Orcia and on the typical strade bianche, up to the ancient village of Murlo, immersed in the dense woods, on the banks of the Crevole river. The itinerary continues then through an enchanting oak forest up to La Befa. A short stretch of the route (ab. 300 mt.) is too slippery to cycle, but the breathtaking views are worth the effort!

Day 3: Buonconvento to Montalcino round tour (24/42 km, +/-588/1177m)
You will cycle through fragrant fields of sunflowers, past Buonconvento, to the heart of the famous Brunello district. You will see the Monte Amiata volcano standing high while at its feet the surrounding countryside is an ocean of olive groves and vineyards. You will then climb up to the fortified city of Montalcino, where you can visit the magnificent 14th century fortress and the Palazzo Comunale and return to Buonconvento cycling on white backroads.

Day 4: Buonconvento to Pienzaa (37 km, +1000m -756m)
Your day will start with a climb up to the famous monastery of Monte Oliveto Maggiore, with its delightful frescoes and the Botanical Garden. After feeding your soul, you will cycle among some hamlets until reaching a row of hundreds of cypresses; it’s an invitation to visit the wonderful Monastery of Sant’Anna in Camprena. Admire the frescoes and end the day sipping a glass of wine in the charming village of Pienza, widely known as the “ideal city of the Renaissance”.

Day 5: Pienza to Bagno Vignoni round tour (27 km, +/-674m)
During this relaxing day you will cycle mostly on country roads across the plains surrounding the medieval village of Bagno Vignoni, where you can rest and relax in its healing thermal waters, as the Romans used to do. The return to Pienza is on rolling hills immersed in the pristine countryside of Val d’Orcia, where you will embrace the real essence of Southern Tuscany.

Day 6: Pienza to Montepulciano round tour (34 km, +/-1000m)
Leaving Pienza, you will cycle along the most famous panoramic roads of Val d’Orcia and pass by the medieval stone village of  Monticchiello. You will then climb an extraordinary limestone ridge and enjoy a breathtaking view. Once you get in Montepulciano, on top of a hill, celebrate with a glass of the famous local Nobile wine. Cycle back to Pienza.

Day 7: Pienza to Buonconvento via Lucignano d’Asso (24 km, +400m -650m)
Today’s route is mainly on dirt roads. You can stop halfway in Lucignano d’Asso, a small village located on L’Eroica cycle route, the famous competition born in Gaiole in Chianti in 1997 and grown into a global movement attracting every year thousands of cyclists and fans from around the world. You will then cycle back to the organic farm of Pieve, in Salti.

Day 8: Buonconvento
After breakfast a short transfer will take you to Buonconvento. End of services.


By choosing to travel by bike with us, you help us make the world a better place: we plant a tree for every trip sold

Why book online on Cyclando?

Because we guarantee you the lowest price and if your tour is not available or confirmed, you can always opt for the refund of the amount paid, or choose another tripfrom the over 800 on the platform.

Our cancellation insurance is the most advantageous you will find around!


Cancel for any reason

Trip cancellation for any documentable reason: pregnancy, illness, work and more, guaranteed.


Coverage of all costs

Full insurance covers all travel costs and penalties from companies, without worries.


Refund in 7 days

With Smart Claims, we guarantee fast refunds in just 7 days for complete peace of mind.

✅ What is included in the trip?

  • Travel/Medical Insurance 24/24
  • Overnight stay and breakfast
  • GPS or navigation APP
  • Luggage transfer
  • Local telephone assistance 7/7
  • Transfer from Buonconvento station to the first hotel (day 1)
  • Transfer from hotel to Buonconvento station (day 8)

❌ What is not included?

  • Transfers not listed as "Included"
  • City tax
  • Tips
  • Journey to/from the starting point of the tour
  • Meals and drinks not listed as "Included"
  • Bike rental
  • Extras
  • Entrance fees, ferries and anything not listed as "Included"
  • Welcome briefing
  • Detailed description and maps of the itinerary

💸 Cancellation fees

  • Time Range
  • Full refund
  • More 31 days of departure
  • 100%
  • From 30 to 31 days before departure
  • 70%
  • From 15 to 30 days before departure
  • 50%
  • From 8 to 15 days before departure
  • 20%
  • Up to 7 days before departure
  • Not refundable

Cycling Tuscany: Val d'Orcia white roads

  • To immerse in the unique landscapes of Val d’Orcia which is Tuscany as you have seen it in your dreams: medieval castles, ancient villages, gorgeous farmhouses, backroads lined with cypress trees, fabulous vineyards, olive groves and golden fields of grain and sunflowers
  • Because Tuscany is the perfect cycling location: the rolling country lanes offer riders a flawless cycling experience whilst the vibrant fields provide you with incomparable views
  • To visit the hot spring town of Bagno Vignoni and discover its its main central square: a pool filled with hot springs water
  • To explore the phenomenal labyrinth streets and artisan workshops of Montepulciano, medieval town of rare beauty surrounded by stunning views on the Tuscan countryside and vineyards
  • To visit Renaissance palaces, Romanesque churches, thermal baths, and prestigious wineries serving the divine local red wine Brunello
  • To Soar up high to fascinating hilltop towns and revel in delight

🙋 Frequently asked questions

  • Can I bring my own bike?

  • What kind of assistance will I have during the trip?

  • How do I know if a tour is within my capabilities?

  • What is the cost of renting bicycles?

  • Are rented bikes equipped with accessories like lights or bags?


Organized by


S-Cape Italy

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Starting from 880per person

stariicon5.0/5on15 reviews

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Minimum participant number: 1




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