Permanent Route of the Heroic in 4 stages

Name: Permanent Route of the Heroic in 4 stages
Brand: Cyclando
Price: 801 EUR
Availability: InStock

Toscana

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Tour

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

Duration

6 days

Distance

206Km

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 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 31 to 30 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

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.