Permanent Route of the Heroic in 4 stages

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


6 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 in Siena. After settling your luggage, you will be given directions on how to best tackle each single stage.

Day 2:  La Val d’Arbia and Montalcino (56 km; +/-1150 m)
After 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 you will intertwine your route with that of the Via Francigena. Later your journey will resume along one of the most challenging sections of the permanent course of L’Eroica, on the beautiful and panoramic hills that produce Brunello di Montalcino wine. Montalcino is a delightful village that deserves a visit and from which to admire the beautiful landscapes that open from the walls of the village. Free dinner and overnight stay in a hotel located in the historic center of Montalcino.

Day 3: Val d’Orcia and Crete Senesi (63 km; +/-1030 m)
The descent from Montalcino will first immerse you in magnificent vineyards, then let you delight in incredible ups and downs of unspoiled and gentle hills that will take you to Lucignano d’Asso, where you can stop for a typical Tuscan snack. After passing Buonconvento, you will continue your pleasant ride surrounded by the characteristic landscapes of the Crete Senesi, in a sparsely populated area, but offering breathtaking panoramas and immersion in the typical Sienese countryside. 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 Accona desert, surrounded by the rugged landscape of the Crete Senesi. Free dinner and overnight stay in a typical Tuscan farmhouse.

Day 4: Monte Sante Marie and Chianti (53 km; +/-1230 m)
Shortly after leaving Asciano, the route will get challenging, you will have to face the stunning ups and downs of Sante Marie, also famous in the shots of the now classic Strade Bianche, towards Torre a Castello. Once past Torre a Castello, you will arrive at Castelnuovo Berardenga, your gateway to Chianti, one of the wine production areas among the most famous in the world for the quality of the wines and for the beauty of the landscapes. The landscape will be an alternation of vineyards as far as the eye can see, charming villages and farms, which can offer a wide choice of typical products, wine and oil tastings, temptations that will sweeten your journey and your palate. Later you will cross Radda in Chianti, which certainly deserves a visit for its charming old town and where you can enjoy a Chianti wine tasting or a leisurely lunch among its typical streets. Free dinner and overnight stay in a hotel. 

Day 5: Gaiole in Chianti and Brolio Castle (47 km; +/-800 m)
After a hearty breakfast, you will leave Radda and head towards Gaiole in Chianti, historic town of L’Eroica. You will cycle in the eastern part of Chianti, facing magnificent climbs among the cypresses until you reach one of the most beautiful symbols of Chianti and L’Eroica, Brolio Castle, from which you can admire one of the most fascinating passages of the route. Leaving Chianti behind, you will start, near San Giovanni a Cerreto, to see glimpses of Siena, one of the most beautiful medieval cities in Italy. The visit of this magnificent city with its Cathedral, Piazza del Campo, the perfectly preserved medieval old town and much more will leave you speechless making your holiday special.

Day 6: 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
  • GPS or navigation APP
  • Luggage transfer
  • Local telephone assistance 7/7
  • 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"
  • 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 4 stages

  • To visit the Duomo, Piazza del Campo and the beautiful medieval center of Siena
  • To surround yourself with the spectacular landscapes of Crete Senesi and Val d'Orcia
  • To touch along the way scenic Tuscan villages like Montalcino, Gaiole and Radda in Chianti
  • To cycle through the boundless vineyards of Chianti and taste its quality wines
  • To train on different types of terrain bringing yourself on the classic White Roads
  • To cross the Tuscany by bike on the historic 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?


Organized by


Anima Toscana

Best Price Guaranteed!

Starting from 701per person

stariicon4.9/5on15 reviews

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Minimum participant number: 2




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