Permanent Route of the Heroic in 3 stages

Name: Permanent Route of the Heroic in 3 stages
Brand: Cyclando
Price: 663 EUR
Availability: InStock

Toscana

Look at the map

See all the photos

Look at the map

Tour

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

Duration

5 days

Distance

217Km

Self-guided

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.

Ring

The starting point is the same as the ending point, with overnight stays in different hotels and daily stages.

Description

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
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 31 to 30 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

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?
Of course! You can participate in any tour with your own bicycle or rent one. However, we recommend renting because not all spare parts are the same, and only with our bikes can we guarantee the best mechanical assistance.
What kind of assistance will I have during the trip?
You will always have an emergency phone number to refer to. In self-guided trips, you should be able to perform minor repairs, like replacing a tube in case of a puncture, or fixing a dropped chain, but you can always count on local assistance for more serious breakdowns.
How do I know if a tour is within my capabilities?
We classify tours on a scale from 1 to 5 based on length, elevation, and complexity of the itinerary, but if you have doubts, contact us and we will help you find the most suitable journey for you.
What is the cost of renting bicycles?
The rental cost varies depending on the bicycle model and the duration of the tour. For some tours, we offer the possibility to rent different types of bicycles. During the purchase process for each route, you will be asked to indicate your preferred bike type and the corresponding price will be shown, so you can choose freely and without surprises.
Are rented bikes equipped with accessories like lights or bags?
Yes, rented bicycles are equipped with all necessary accessories to comply with road traffic regulations (lights, bell, etc.). A lock, repair kit, and a bag to carry everything you need for a day in the saddle are always included in the rental. Additionally, we offer the option to request extra accessories based on your needs.