Permanent Route of the Heroic in 3 stages

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


5 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!

4/5 Medium-Easy

Moderate-Difficult, between 50 and 100 kilometers per day with an elevation gain between 700 and 1300 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 overnight stay in a star hotel located just steps 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 centre. Upon arrival, you will be given instructions on how to best tackle every stage.

Day 2: The Val d’Arbia and Montalcino (74 km; +/-1480 m)
Leaving the city of Siena, you will face one of the characteristic stretches of the route, the one between Colle Malamerenda and Radi, immersed in the gentle Sienese hills dotted with farmhouses and historic villages, where your route will intertwine with the Via Francigena. The village of Murlo will provide the backdrop to the easiest part of the stage, but past Bibbiano, you will face one of the most challenging stretches of dirt road on the permanent route of L'Eroica, which will take you panoramically through the rolling hills of the Brunello di Montalcino wine-producing area. Montalcino is a delightful village that deserves a visit: admire the beautiful views that open up from the village walls. Leave the Brunello hills behind and head towards the Val d'Orcia, to reach the village of San Quirico d'Orcia, the final destination of the first stage.

Day 3: The Crete Senesi and Monte Sante Marie (72 km; +/-1400 m)
The first part of the day involves a pleasant cycle, surrounded by the characteristic landscapes of the Val d'Orcia and the Crete Senesi, in a sparsely populated area but offering breathtaking views of the typical Sienese countryside, until you reach Buonconvento, one of the most beautiful villages in Italy. After Asciano, the route becomes challenging, tackling the delightful ups and downs of Sante Marie, also famous for the classic Strade Bianche, towards Torre a Castello. Once past Torre a Castello, you will reach Castelnuovo Berardenga, your gateway to Chianti. A route option will allow you to reach the Abbey of Monte Oliveto, located on a hilltop covered with cypresses, in a suggestive position in the middle of the Accona desert, 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 the Brolio Castle (77 km; +/-1360 m)
The final stage will take you to Chianti, one of the most renowned wine-producing areas in the world, renowned for the quality of the wine and the beauty of the landscapes. The scenery will alternate between endless vineyards and woodland, continuing through small villages and agricultural businesses, offering a wide selection of local 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 charming old town and where you can take advantage of a Chianti wine tasting or a relaxing lunch amid its characteristic alleys. Once you leave 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 the Brolio Castle, which with its ascent through the cypresses, passing under the Castle's walls and the descent over stunning landscapes and breathtaking vineyards, represents one of the most fascinating scenarios of the route. Dating back to the 11th century and owned by the Ricasoli family 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
  • 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"
  • Welcome briefing

💸 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 stages

  • To penetrate the heart of the Lands of Siena crossing the Chianti, the Senesi Clays and the Val d'Orcia
  • To admire along the way the beautiful Tuscan villages
  • To change terrain crossing other exceptional routes like that of Strade Bianche
  • To lean from the Brolio Castle and enjoy a breathtaking view of the rows of vineyards below
  • To train in Tuscany by bike on the legendary Permanent Route of the Heroic

🙋 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?


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Starting from 660per person

stariicon4.9/5on15 reviews

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Minimum participant number = 2




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Chosen by 21 people

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VAT ID: 03880320365

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