Tour Il Piu’ HEROIC

It starts on Saturday from Radda in Chianti, After a welcome dinner on Friday evening.

The first day touches Siena, Montalcino and ends in San Quirico d’Orcia, where we will ascertain in a typical room in the area and sleep at the hotel, both carefully selected by our local guide.

Sunday we will cross the Sienese Crete, Stopping for a coffee in Asciano and final lunch at the historic Villa Cerna in Castellina in Chianti.

A path of 310 Km on simple panoramic and dirt roads, Perfect for each type of motorcycle.

The tour is organized for small groups, massimo 8 motorcycle. Possibility to follow the solo tour, following the GPX tracks that we will provide.

🛵 Your motorcycle is required: There is no rental by the organization.

What is included in the tour

- Welcome dinner on Friday in Radda in Chianti
- 2 days of tours with local guide on traced route (GPX)
- Overnight at the hotel on Friday and Saturday
- Dinners in typical Tuscan restaurants (Friday and Saturday)
- Saturday and Sunday lunches
- Luggage transport
- Tour T -shirt + motorcycle table
- Guaranteed assistance along the route in case of unexpected events

What is not included

- Fuel
- Overnight in a single room (Available on request)

📩 Group trips and looking for different dates?
Write us a booking@chiantilive.it, we find the right solution for you.


Full package: Ball € 380 - Accompanying € 280
- Overnight stay on Friday in the hotel 4 stars, double room in Radda in Chianti
- Dinner in a typical restaurant on Friday evening
- Saturday lunch and tasting at Fattoria Brunello Montalcino
- Overnight stay on Friday in the hotel 4 stars, double room in Pienza
- Dinner in a typical restaurant on Friday evening
- Luggage transport
- Guide

Solo trip: Ball € 120 - Accompanying € 110
- No driving
- Dinner in a typical restaurant on Friday evening
- Saturday lunch and tasting at Fattoria Brunello Montalcino
- Dinner in a typical restaurant on Friday evening
- GPX file of the route


🗓️ Tour program - the most heroic
All activities base at the ORLANDO Glamping in Chianti.

📍 Friday 9 May

16:00 – 18:00 | Participants and check-in welcome at the hotel

20:30 | Welcome dinner and briefing on the route

🏍️ Saturday 10 May

08:30 | Departure from the hotel

09:30 | Coffee stop in Piazza del Campo, Siena (For group participants with guide)

12:00 – 14:00 | Lunch break in Montalcino

17:00 | Arrival in Pienza and hotel accommodation

20:00 | Dinner in a typical restaurant in Pienza

🏁Sunday 11 May

09:00 | Departure from Pienza

13:00 | Arrival in Radda in Chianti

14:00 | Lunch in the vineyard or in the cellar (Only reservation only - not included in the share of the event)


The tour takes place in one of the most beautiful and hospitable territories of Italy.

For this we ask each participant to bring with them not only the desire to guide, but also respect, Curiosity and attention, The distinctive features of every real traveler motorcycle.

Even if each member accepts the Official regulation At the time of registration, We would like to underline some fundamental points:

"The most heroic" is a tourist journey, Not a race.
• The spirit of the tour is made of conviviality, sharing and respect for the local communities that welcome us.
• The organization reserves the right to exclude at any time Anyone who does not respect these values.
We also remember that the whole route takes place on roads open to traffic, asphalted and dirt roads.

Each participant is responsible for his own conduct and must Respect the Highway Code and all the safety and common sense rules.

🚩 All events organized with the name "The classic" are tourist trips officially organized by Chianti Live Srls - Tour Operator.


Participation in the tour The most heroic is limited e accessible only on pre-registration.

This allows us to better organize every detail and guarantee a well -kept welcome for all participants.
The fee includes:
• GPX track of the route
• Travel insurance
Important note: The registration fees they are not refundable.

One is active EUROPE Assistance Travel Policy with covers according to the cancellation policy of Chianti Live Tour Operator.
📞 Contacts for information and reservations:

Claudio Matteuzzi
Tel: 335 37 59 25
Email: booking@chiantilive.it

The places are few, do not wait!

Book now!

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