Permanent Route of the Heroic in 4 Luxury stages

pin-icon Toscana





Look at the mapsmall-map-icon




Bike Tours, Road cycling holidays, E-bike tours


6 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!

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 detailed maps and instructions on how best to tackle each single stage.

Day 2: The Val d’Arbia and Montalcino (56 km; +/-1150 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 Siena hills dotted with farmhouses and historic villages, where you will weave your route with that of the Via Francigena. Subsequently, your journey will resume along one of the most challenging white road sections of the permanent L’Eroica route, on the beautiful and panoramic hills of Vino Brunello di Montalcino production. Montalcino is a delightful village that deserves a visit and from which to admire the beautiful views 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 delight you with incredible ups and downs of pristine and gentle hills that will lead 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 an sparsely populated area, but offering breathtaking views and an immersion in the typical Siena countryside. An alternative route will allow you to reach Monte Oliveto Abbey, located on a hill covered with 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 4: Monte Sante Marie and the Chianti (53 km; +/-1230 m)
Immediately after leaving Asciano, the route will become challenging, you will face the wonderful ups and downs of Sante Marie, famous also 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 door to the Chianti, one of the most famous wine-producing areas in the world for the quality of the wines and the beauty of the landscapes. The landscape will be a mix of vineyards as far as the eye can see, lovely villages and farms, offering a wide choice of typical products, wine and oil tastings, temptations that will sweeten your journey and your palate. Afterwards, you will cross Radda in Chianti, which certainly deserves a visit for its charming historic centre, where you can delight in a tasting of Chianti wine or a relaxing lunch among its typical streets. 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, the historic town of L’Eroica. You will cycle in the eastern part of Chianti, tackle 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, near San Giovanni a Cerreto, you will start 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 historic center 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
  • Welcome briefing
  • Detailed description and maps of the itinerary
  • 5 dinners (drinks not included)
  • 4 light lunches

❌ 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 4 Luxury stages

  • To cycle in Chianti, surrounded by lush vineyards, savoring famous wines
  • To visit the Duomo, Piazza del Campo, and the suggestive medieval center of Siena
  • To immerse yourself in the most beautiful landscapes of Tuscany: the Crete Senesi, the Val d'Orcia and the Val d' Arabia
  • To ascend to the picturesque village of Montalcino and taste the typical Brunello
  • To cross other legendary routes like the Via Francigena and White Roads
  • To train on the multiple types of terrain of Tuscany by bike, along the mythical 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



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

© Cyclando 2024 - All rights reserved.


Version 1.19.1

Sign up and receive unique travel offers!

Become part of our community, stay updated on our activities