Permanent Route of the Heroic in 5 Luxury stages

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Bike Tours, Road cycling holidays, E-bike tours


7 days





Travel alone or with your loved ones, but with the support of a specialized guide. The perfect organization and safety in a single experience!

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
Individual arrival, dinner and overnight stay in a 3-star hotel located just a few steps from the historic center of Siena. Upon your arrival, you will receive road books and detailed maps.

Day 2: Val d’Arbia and Montalcino (49 km; +/-1130 m)
Upon leaving the city, you will tackle one of the most typical gravel road stretches of the Permanent Route of "L'Eroica", the one between Colle Malamerenda and Radi, immersed in the rolling Sienese hills dotted with farmhouses and historic villages. Here the L’Eroica route intersects the Via Francigena. The small village of Murlo will provide the backdrop for the easiest part of your journey. The second part of the stage will take you to the beautiful and panoramic hills where the Brunello di Montalcino wine is produced, along one of the most challenging gravel road stretches. Montalcino also deserves a visit, to admire the beautiful panoramas from the walls of the old town centre. Free dinner and overnight stay in a three-star hotel in the center 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 be a delightful dive into vineyards, then a route that unfolds in the undulating hills, taking you to Lucignano d’Asso, where you can take a break for a typical Tuscan snack or simply fill up your water bottle before reaching the stage finish. With a small detour from the original route, you'll have the chance to cycle in the heart of the Val d’Orcia, a UNESCO Heritage site. Along the way, you can visit San Quirico d’Orcia and Pienza, two villages rich in history and charm. Free dinner and overnight stay in a typical Tuscan farmhouse located in the southern part of the L'Eroica route, with an indoor and outdoor pool, spa, and riding stable. The restaurant serves genuine dishes, typical of the Tuscan culinary tradition, based on organic products.

Day 4: The Crete Senesi and Monte Sante Marie (44 km; +/-840 m)
Surrounded by the unique landscapes of the Crete Senesi, you will pedal through a sparsely populated area, offering breathtaking views of the hills and Siena. It will be essentially an immersion into typical Sienese countryside. After Asciano, the route will become challenging, across the beautiful up and down hills of Sante Marie, famous gravel stretch of the classic White Roads. Once past Torre a Castello, you will arrive in Castelnuovo Berardenga, your gateway to Chianti. An alternative route will allow you to reach the Abbey of Monte Oliveto, situated on a height surrounded by cypresses, in a striking position, in the middle of the Accona Desert, surrounded by the rugged landscape of the Crete Senesi. Free dinner and overnight stay in a typical Tuscan farmhouse.

Day 5: Chianti (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 production areas in the world for the quality of its wines and the beauty of its landscapes. Here you'll find a succession of vineyards as far as the eye can see, small villages and farms, offering a wide choice of typical products, wine and oil tastings, that will sweeten your journey and palate. After reaching Vagliagli, the route will take you to Castellina in Chianti. We recommend visiting this charming medieval village.

Day 6: Castello di Brolio and Siena (46 km; +/-800 m)
In the first part of the stage, you'll tackle the gentle climb that will lead you to one of the symbols of Chianti and L'Eroica, the Castle of Brolio, that with the ascent through the cypresses, the passage under the walls of the Castle, and the descent onto breathtaking panoramas, represents one of the most fascinating parts of the Permanent Route. Before heading to Siena, you will have the chance to visit the Castle of Brolio, the heart of the wine making estate that dates back to the 11th century and has been owned by the Ricasoli family since 1141. Leaving behind Chianti, near San Giovanni a Cerreto, you will begin to see glimpses of Siena, one of the most beautiful medieval cities in our country. A visit to this magnificent city will make your holiday special: the Duomo, Piazza del Campo, the perfectly preserved medieval historic center and much more will leave you in awe.

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

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
  • Luggage transfer
  • Local telephone assistance 7/7
  • Welcome briefing
  • Detailed description and maps of the itinerary
  • GPS or navigation APP

❌ 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

Permanent Route of the Heroic in 5 Luxury stages

  • To visit the Duomo, Campo Square, and the beautiful medieval center of Siena
  • To enjoy suggestive views of Chianti, the Crete Senesi and the Val d'Orcia
  • To combine the beauty of cycling with a passion for great wines by giving yourself a Wine Tour with a tasting at the Brolio Castle
  • To completely immerse yourself in the beauty of the landscapes and the legendary charm of the route
  • To cross the best of Tuscany by bike with this All Inclusive version of the Permanent Route of the Heroic which will allow you to leave all thoughts at home

Package only on request.

Some of our tours are not available or bookable at the moment. If you are interested in this tour, then ask our team for more information on upcoming availability, or on a similar tour available or bookable immediately!

🙋 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

Cyclando srl

Tour operator with Europe Assistance RC Insurance 4249713 - Registered with the Guarantee Fund with A.I.A.V. Associazione Italiana Agenti di Viaggio trough IL SALVAGENTE s.c. a r.l.. All rights reserved.

VAT ID: 03880320365

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