Permanent Route of the Heroic in 3 Luxury stages

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Bike Tours, Road cycling holidays, E-bike tours


5 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!

5/5 Challenging

Difficult, between 60 and over 100 kilometers per day with an elevation gain between 800 and over 2000 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 at leisure and accommodation in a 3-star hotel located a short walk from the historic center of Siena. Staying in Siena gives you the opportunity to dedicate part of your day to visiting the Cathedral, Piazza del Campo, and the medieval historic center. Upon your arrival, roadbooks, detailed maps, and instructions on how to best tackle each stage will be given to you.

Day 2: Val d’Arbia and Montalcino (74 km; +/-1480 m)
After leaving the city of Siena you will tackle one of the characteristic stretches of the route, that between Colle Malamerenda and Radi, immersed in the gentle Sienese hills dotted with farmhouses and historic villages, where you will intertwine your path with the Via Francigena. The village of Murlo will act as a backdrop to the easiest part of the stage, but past Bibbiano you will face one of the most challenging white road sections of the permanent route of L'Eroica, which will lead you to the beautiful and scenic hills that produce Brunello di Montalcino wine. Montalcino is a delightful village that is well worth a visit: admire the beautiful views that open up from the walls of the town. Leave the Brunello hills behind and head to the Val d'Orcia to reach the village of San Quirico d'Orcia, the final destination of the first stage.

Day 3: Crete Senesi and Monte Sante Marie (72 km; +/-1400 m)
The first part of the stage involves a pleasant ride, surrounded by the characteristic landscapes of the Val d'Orcia and the Crete Senesi, in a sparsely populated area that offers breathtaking views of the typical Sienese countryside, until reaching Buonconvento, one of the most beautiful villages in Italy. After Asciano, the route becomes challenging, facing the beautiful slopes of Sante Marie, also famous for the classic Strade Bianche, towards Torre a Castello. 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 hill covered with cypresses, in a suggestive position in the middle of the Desert of Accona, surrounded by the rugged landscape of the Crete Senesi. Overnight stay in a typical Tuscan farmhouse with a swimming pool.

Day 4: Chianti, Gaiole and Brolio Castle (77 km; +/-1360 m)
The last stage takes you into Chianti, one of the most famous wine producing areas in the world, both for the quality of its wines and for the beauty of its landscapes. The landscape will alternate between vineyards stretching as far as the eye can see and woods, continuing through small villages and farms, which can offer a wide choice of typical products, wine and oil tasting, temptations that will sweeten your journey and your palate. You will cross Radda in Chianti, which will win you over with its enchanting historic center and where you can take advantage of a Chianti wine tasting or a relaxed lunch among its quaint alleyways. Once you have left Radda, you will head towards Gaiole, the town where L’Eroica was born in 1997. The final part of your tour will allow you to reach Brolio Castle, which with the climb among the cypresses, the passage under the castle walls and the descent onto breathtaking views and vineyards, represents one of the most fascinating scenarios of the route. Dating back to the 11th century and owned by the Ricasoli since 1141, it is certainly worth a visit.

Day 5: 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"
  • Bike transfer back from arrival to starting point

💸 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 3 Luxury stages

  • To contemplate the bright green of the vineyards from the top of Brolio Castle
  • To delve into the heart of the Siena lands crossing the Chianti, Crete Senesi and the Val d'Orcia
  • To admire along the way the beautiful Tuscan villages
  • To change terrain crossing other exceptional routes such as that of Strade Bianche
  • To train in Tuscany by bike on the legendary Permanent Route of the Heroic

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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