The Permanent Route of The Heroic in 5 stages

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Bike Tours, Road cycling holidays, E-bike tours, Gravel bike tour, MTB cycling holidays


7 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: Siena
Arrive individually, with dinner and overnight stay in a hotel located just a few steps from the historic center of Siena. On your arrival, you will be given instructions on how to best tackle each single stage.

Day 2: Arbia Valley and Montalcino (55 km; +/-1130 m)
As soon as you leave the city, you will tackle one of the most characteristic white road sections of the Permanent Route of L'Eroica, the one between Colle Malamerenda and Radi, set among the gentle Sienese hills dotted with farmhouses and historic villages. Here the L’Eroica route crosses the Via Francigena. The small village of Murlo will be the backdrop to the easiest part of your ride. The second part of the stage will lead you to the beautiful and scenic hills where the Brunello di Montalcino wine is born, passing along one of the most demanding white road sections. Montalcino is also a charming village that is worth a visit, also to admire the beautiful views that open up from the walls of the village. Dinner at your leisure and overnight stay in a hotel in the centre of Montalcino.

Day 3: Val d’Orcia (35 km; +/-560 m) or Val d’Orcia and Pienza (53 km; +/-560 m)
The descent from Montalcino will first be a delightful plunge into the vineyards, then a journey that will stand out in the ups and downs of pristine and magnificent gentle hills that will bring you to Lucignano d'Asso, where you can stop for a typical Tuscan snack or just refill your water bottle, before reaching the final point of the stage. With a small deviation from the original route, you will have the opportunity to cycle in the heart of the Val d'Orcia, a UNESCO World Heritage site. Along the route, you can visit San Quirico d'Orcia and Pienza, two villages rich in history and charm. Dinner at your leisure and overnight stay in a typical Tuscan farmhouse, located in the southern part of the L'Eroica route, equipped with indoor and outdoor pools, spa and riding school. At the restaurant, genuine dishes typical of Tuscan culinary tradition are served based on organic products.

Day 4: Crete Senesi and Monte Sante Marie (44 km; +/-840 m)
Surrounded by the characteristic landscapes of the Crete Senesi, you will ride through a sparsely populated area, offering breathtaking views of the hills and Siena. It will be mainly a dip in the typical Sienese countryside. After Asciano, the course becomes demanding, on the beautiful ups and downs of Sante Marie, a famous dirt road section of the classic Strade Bianche. Once you have passed Torre a Castello, you will reach Castelnuovo Berardenga, your gateway to Chianti. An alternative route allows you to reach the Abbey of Monte Oliveto, located on a hill framed by cypresses, in a suggestive position, in the middle of the Accona desert, surrounded by the rugged landscape of the Crete Senesi. Dinner at your leisure and overnight stay in a typical Tuscan farmhouse.

Day 5: The Chianti area (40 km; +/-750 m)
The fourth stage on the Permanent Route of L'Eroica will take you to Chianti, one of the most famous wine-producing areas in the world for the quality of the wines and the beauty of the landscapes. Here everything is a succession of vineyards as far as the eye can see and woods, small villages and farms, which will offer you a wide choice of typical products, wine and oil tastings, temptations that will sweeten your journey and your palate. Once you reach Vagliagli, the route will take you to Castellina in Chianti. We recommend a visit to this charming medieval village.

Day 6: Brolio Castle and Siena (46 km; +/-800 m)
In the first part of the stage, you will face the sweet climb that will lead you to one of the symbols of Chianti and of L'Eroica, the Brolio Castle, which with its ascent among the cypresses, the passage under the walls of the Castle and the descent on breathtaking views, represents one of the most fascinating stages of the Permanent Route. Before directing to Siena you will have the opportunity to visit the Brolio Castle, hub and symbol of the company, dating back to the 11th century and owned by the Ricasolis since 1141. Leaving Chianti behind you will start, near San Giovanni a Cerreto, to see glimpses of Siena, one of the most beautiful medieval towns in our country. The visit to this magnificent city will make your holiday special: the Duomo, Piazza del Campo, the perfectly preserved medieval historical center and much more will leave you speechless.

Day 7: Siena
After breakfast, end of services and individual departure.

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

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✅ 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
  • Welcome briefing
  • Detailed description and maps of the itinerary

❌ 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"

💸 Cancellation fees

  • Time Range
  • Full refund
  • More 31 days of departure
  • 75%
  • From 30 to 31 days before departure
  • 50%
  • Up to 7 days before departure
  • Not refundable

The Permanent Route of The Heroic in 5 stages

  • To live the myth of The Heroic which, divided in this way into convenient stages, becomes accessible to all, at any time of the year
  • To appreciate Tuscany in all its Tuscanity by pedaling from the Terre di Siena to Chianti, from the Crete Senesi to the Val d'Orcia
  • To pedal on the hills where the great Tuscan wines such as Brunello di Montalcino and Chianti are born, and perhaps reward yourself with some stops for a tasting in the wine cellars
  • To indulge in some deviation from the historic route and, in the heart of Val D'Orcia, visit San Quirico d'Orcia and Pienza, charming villages rich in history
  • To not miss anything and also cover a short section of the classic Gran Fondo Strade Bianche
  • To surrender to the breathtaking landscapes of Tuscany by bike and thanks to the short stages, as well as living the myth of The Heroic, giving oneself time to fully enjoy the places visited

🙋 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


Anima Toscana

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Starting from 839per person

stariicon4.9/5on15 reviews

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Minimum participant number: 2




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