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Chianti - Tuscany

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Self-Guided Eroica Tour

Self-guided Eroica Tour.
March October Every day all year round

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Self-guided Eroica cycling Tour on a road bike

L’Eroica is an annual non-competitive cycling event which takes place since 1997 in the province of Siena, Italy. The theme of the event is vintage cycling, with participants using vintage (= pre-1987) bikes, accessories, and clothing, and the route often includes unpaved roads. It is held on the first Sunday of October.

The whole itinerary of the Eroica cycle event (plus part of Chianti Fiorentino) is tackled in three stages with stops in Siena, Radda in Chianti, and Buonconvento; the tours are difficult, both for the distances and the accumulated climbs and for the long parts on white roads that turn out to be more challenging to ride than asphalt.

Cycling in Italy is great, especially in the beautiful regions of Tuscany and Chianti. You will discover the peaceful countryside roads with very little traffic when you climb the rolling hills of Chianti. Beyond all cycling activities, you also visit the vineyards of the Castello di Brolio

The race starts every year from Gaiole in Chianti and reaches Siena only after some kilometers. Since it is much easier to reach Siena by public transport it’s better to start the tour here. You will have time to visit this wonderful town on arrival day and on the last morning. Despite this change, the whole circuit will be completely done.

Don’t miss the opportunity and immerse in this wonderful Eroica cycling tour

  • Experience this legendary cycling event
  • Stunning scenery along the way
  • 4 nights in charming 3 * hotels with double rooms with breakfast
  • Cycling the full Eroica in 3 stages
  • Siena, Radda in Chianti and Buonconvento visits
Day 1
Check in
Independent arrival in Siena and settling into the hotel. Siena can be reached by local trains from Pisa and Florence, where Tuscany's main airports are. Private minibus transfers to other destinations and airports can be arranged on request.
Day 2
Siena - Montalcino - Pieve a Salti 87km
You’ll leave Siena riding happily on local and white roads along the gentle hills south of town to reach Buonconvento: the second part of the route can be circular, passing through Montalcino at the southernmost point, then taking in Val d'Orcia before heading back on unpaved roads to the wonderful accommodation lost between "Crete Senesi" and Val d'Orcia, a perfect place where relaxing in the swimming pool or simply on a meadow, far from the "civilization" (and taste great Tuscan food). The most challenging stretch of the day will be the long but enjoyable ascent to Montalcino, a land devoted to producing the excellent Brunello wine which is a large part of everyday life here.
Day 3
Buonconvento - Castelnuovo Berardenga - Radda 79km
You turn northwards and head into the Crete Senesi: here the hills are mostly bare and gently undulating as far as the eye can see, dotted with lone trees and isolated farmhouses on the hilltops, and in places clay turns the soil blueish-grey, giving the landscape a lunar feel. There are so few buildings in sight that man seems almost absent. The white roads occasionally become steep and graveled, more difficult to ride, but at the end of every struggle you are rewarded with a breathtaking view. This is perhaps the moment when we feel the most "heroic", in close contact with the land. We will pass Asciano, Castelnuovo Berardenga, and a few other towns on the way to the Chianti region, the beloved vineyards; here you find a completely different landscape and accommodation in Radda in Chianti.
Day 4
Radda - Greve in Chianti - Castello di Brolio - Siena 84km
In the Chianti area, it is easy to come across authentic and fascinating little towns; our final stage shows us the best-known towns and wineries such as Panzano, Greve, Gaiole in Chianti, Castello di Lemole and Castello di Brolio, to name but a few places worth a visit. Your aim is to reach our final destination of Siena but pick up the nuances of this landscape along the way. As you mentioned before, the point of sub-dividing the stages is partly to follow the route of l'Eroica, but also to create different "settings", so that each stage brings new surprises and you reach your final destination with a big smile on your face, proud of our achievement.
Day 5
Departure day from Siena
From Siena, the railway line (and bus routes) take you to Pisa, Florence, and Rome, with their international airports. Just outside the city, you can hire a car from Hertz or Europcar. Private minibus transfers to other destinations and airports can be arranged on request.

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  • All prices are based on double rooms.
  • For bookings and inquiries contact us at

Extra Information

  1. Fill out and submit the online booking request or send an email to
  2. We tend and try to send all over within 48 hours.
  3. Please do not make travel plans until you receive our confirmation.
  4. Please be advised that we make every effort to ensure that all the information given on this site is accurate. All statements and information have been researched and supplied by third parties.
  5. The information given is accurate and reliable, to the best of our knowledge. Should errors be found, we will rectify them as quickly as possible. However, we accept no responsibility for errors or inaccuracies.
  • Accommodation in a double room with private facilities
  • Breakfast
  • Welcome briefing at the departure hote
  • Luggage transport from hotel to hotel
  • Detailed travel documents (maps, route description, locations, important phone numbers)
  • Telephone assistance service for the duration of the tour
Bike Rentals
  • Road Bike +190 euro
  • Vintage Bike +150 euro
  • E- Road Bike +265 euro
  • Gravel Bike on request
  • Arrival at the starting point of the tour
  • Return trip at the end of the tour
  • Lunches, dinners, and drinks
  • Tourist taxes and all extras in general
  • High season supplement from 15/5 to 15/10 100 euro
  • Single room surcharge 200 euro
  • Carbon road bike Disc Ultegra 190 euro
  • E road bike 265 euro
  • Vintage Bike 150 euro
  • Transfer from Pisa airport or railway station to Siena € 350
  • Transfer from Florence airport or railway station to Siena € 190
  • Transfer Roma airport or railway to Siena € 500




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