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Home » Tour 2017 » Eroica: a leggendary road

Eroica: a leggendary road


A magnificent immersion in Chianti Wine’s lands through the soft hills of Tuscany

Dates upon request

Everybody has somehow heard something about L’Eroica … But what is it, exactly?
Gigi Garanzini, a sport jouralist describes it this way: “Just forget about superhuman performances, last generation equipment or doping. Tuscany’s roads welcome a cycloturistic event for old-time bikes only. It as not a race but a happy celebration of ‘how it used to be’, seasoned with bread and salami!”.

L’Eroica, as an event, takes place the first Sunday of October, and you can participate (there are four itineraries: 38 – 75 – 135 – 205 km) only of you have got a bike that dates back to the 80’s or earlier.  Those who did it, say it is a very nice party amoung old bikes, polished as new for the occasion, aged wollen tshirts, pull-ups that, like traditional ‘osterie’, offer you the best typical food served by shephards and countrymen. But must of all a lot of participants, of all kinds, from all nations, people who want to have fun by bike, taking it as a good way to spend time, in good company, and absolutely not like a race.

But it is not just this. The event described above was created 15 years ago from a group of friends from Siena that shared their passion for sport and for their land; they therefore decided to lauch this idea, the aim of their effort was to save a paths and dirt roads that were to be paved with asphalt. Those roads, in fact, are a very important part of the typical landscape of this region.
The manifestation got more and more important, and caught national and international mass media attention; the idea got then supported by funds of the Catasto strade bianche project that worries about conserving, mapping, and in general wants to revalue those forgotten parts of history.

Thanks to the work of many volunteers it is today possible to bike those roads of the Eroica itinerary. Then, let’s get ready to follow the big bordeaux “E” along the 205 km initerary, through the long roads and up and down the sweet hills. But it is impossible to get tired: everything is too beautyful to stop. Those wines, the woods, the country, the old castles or forgotten countryhouses and following the most traditional roads of the people that live this breathtaking nature.

Leaving from Radda, one of Chianti’s most beautiful towns, we will then stop in Buonconvento a small town rounded by its medieval walls. Next day by a short deviation we will then stop for the night in Mosanella’s Castle, its luxurious silece will bewitch us. Then we’ll follow our original track to close the circle we began, back to Radda, with the last up hill shot.

Sites of interest

UNESCO World Heritage Sites: Siena
Italy’s most beautiful villages: Buonconvento
Touring Club Italiano Orange Flag: Castelnuovo Berardenga, Montalcino, Murlo, Radda in Chianti.


This trip has already been tested and can be adapted to small or bigger groups. We propose  guided tours leaded by our guides who speak English, German, French, Spanish and Portuguese. We can provide this trip also without leaders as long as the group can follow the tracks using a gps since itineraries develop on broads that are not always easy to find.

On demand we can also provide other services as, for instance, a bus following the group and much more. Big groups are kindly invited to book in advance. 

To contact us:
Speaking: English – Spanish – French
Anna Magrin – anna@simonettabiketours.it

Speaking: German – Portuguese
Elisa Zambelli – elisa@simonettabiketours.it

Services included in our previous tours

  • 3 nights with breakfast in three and four stars hotels and in Modanella’s Castle.
  • 3 three-course-dinners with typical local recipes, with a drink (1/4 liter wine or 300 cl beer), tap water and bread included.
  • 3 packed lunches, which include sandwiches, fruit, a dessert, 1/2 liter water.
  • 3 tour guides, 2 by bike and one driving the off-road vehicle (with groups from 12 to 17 participants only 2 staff members will guide the tour).
  • 3 hotel city tax.
  • Agency van, which follows the whole tour in order to guarantee: the luggage transport service, the picnics for lunch and snacks, the availability and the assistance during the tour.
  • Colour tour handbooks’ with historical and artistic information (at the time being available only in Italian).

Extra services

Bike renting. We can provide excellent quality bikes for the entire duration of the tour. Bikes are given and handed in on the spot.


How to Book



Duration: 4 days, 3 nights, 3 biking days

When: to be defined; trip will take place upon groups reservation, small or big.

Difficulty: advanced

Where: Italy > Tuscany

Tour description: The tour is a 3 days bike round route leaving and arriving in Radda. We will follow the full eroica’s track, mostly without any traffic, deviating only to sleep at Modanella’s Castle. We will ride on well kept dirt roads, although some sections could be in worse condition. Up and down hills are very frequent, mostly sweet, some harder.



Day 1
Independent travel to Radda in Chianti.

Day 2
Radda in Chianti > Buonconvento
82 km – about 1.200 meters height difference – up hill itinerary.

Day 3
Buonconvento > Castello di Modanella
100 km – about 1.450 meters height difference – up hill itinerary.

Day 4
Castello di Modanella – Radda in Chianti
70 km – about 1.000 metres height difference – up hill itinerary.
Back to Radda in Chianti, arrival time 5 p.m.

Download Pdf program