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Villages, iconic roads and vineyards – Grand Tour of Chianti

Di Chap (CC BY-NC-ND 2.0)

Villages, iconic roads and vineyards – Grand Tour of Chianti

Bike Touring Collection by Francesco | Cyclo Ergo Sum



3-3 h

/ day

65.7 mi

6,475 ft

6,450 ft

Oh how beautiful is youth
And quickly does it flee,
Be happy if you want to,
For tomorrow may not come.

This is how Lorenzo de' Medici's famous ‘Canzona di Bacco’ begins. It’s the best-known of the Carnival Songs and a call to fully enjoy the joys of life (the senses, beauty, love) in the knowledge of their fleetingness.

On your bike, you can follow Lorenzo de’ Medici’s call on the Grand Tour of Chianti. The route takes you to unforgettable places in one of Italy’s most loved areas. You’ll
pedal on low traffic roads with your eyes on the beautiful hills that straddle Florence and Siena. Food and wine isn’t missed off the itinerary either.

Starting from Castelnuovo Berardenga, you'll ride through some of the Sienese Chianti villages as you trace one of the most famous routes in Tuscany, if not the entire Bel Paese – L'Eroica. L’Erocia is an annual non-competitive cycling event where participants ride vintage bikes.

The Chianti Grand Tour route is 106 kilometres (66 mi) long and, just like a good DOCG wine, you can choose to finish it in one ‘sip’ or take your time. As many of us enjoy bike holidays at a slower pace, I recommend splitting the route into at least two stages, each with around 1,000 metres (3,200 ft) of ascent. That way you won't get drunk on fatigue or struggle to find hospitality and numerous options for tasty food and wine.

Some typical villages of the Chianti area of Siena such as Castellina, Radda in Chianti, the steep pass of Monte Luco lie en route. You’ll also explore the small town of Gaiole in Chianti, the birthplace of Eroica in 1997, a magical cycling event that combines challenging routes, magnificent scenery, and unforgettable refreshments.

So treat yourself, indulge in the local food and drink and enjoy the well-maintained paved roads between short climbs and descents. It’s a feast for your eyes and your tastebuds, as you enjoy the scenery and traditional Tuscan flavours such as soups or sliced meats.

You can reach the starting point by car or by alighting the Siena-Rome train at Castelnuovo Scalo and pedalling the last few kilometres to Castelnuovo Berardenga. Alternatively, you can take the train from Siena to Palio and join the track at Ponte a Bozzone.

You can ride on any type of bicycle with reasonable gearing for climbs. It's best to ride the Grand Tour of Chianti from March to November, aside from the hottest months. The climbs are relatively tough and high temperatures only make them harder.

Look forward to an unforgettable adventure, full of excitement and good food: enjoy your trip to the land of Chianti!

On The Map


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Grand Tour del Chianti – percorso completo

65.7 mi

6,475 ft

6,475 ft

Last updated: July 26, 2023

Plan your own version of this adventure in the multi-day planner based on the stages suggested in this Collection.

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  1. Map data © OpenStreetMap contributors

    Stage 1: Castelnuovo Berardenga to Radda in Chianti – Grand Tour of Chianti

    34.3 mi
    8.9 mph
    3,150 ft
    2,550 ft
    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

    The ring of the Grand Tour of Chianti begins in Castelnuovo Berardenga, a small town in Chianti with churches that date back as far as the seventeenth century, majestic villas with gardens such as Villa Chigi Saracini, the civic tower that soars above the stone houses and the interesting Museo del Landscape

    translated byView Original


  2. 03:36
    31.4 mi
    8.7 mph
    3,325 ft
    3,900 ft
    Expert bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

    The "eat and drink" of the Chianti Grand Tour also continues on this second day, from Radda in Chianti to Castelnuovo Berardenga. In the first part of the stage there are no particularly challenging altitude differences: you can fully enjoy the panorama that surrounds you.


    Around kilometer 22, make a

    translated byView Original



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Collection Stats

  • Tours
  • Distance
    65.7 mi
  • Duration
    07:28 h
  • Elevation
    6,475 ft6,450 ft

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