Via Gruccia 23/G Int.11, 52027 San. Giovanni Valdarno (AR) Italy
P.Iva & C.F: 02306110517

Tour Operator n° – 41650

Chianti villages West – road cycling

starting point

Tuscany bicycle, Gaiole in Chianti


195 per person

(please note: pick up may be arranged from other places at an additional fee. Email us for details)


7 hours

elevation gain

1140 mt

distance biked

50 - 70 km


Chianti classico wine region of Tuscany

type tour

Road biking

bike type

Full carbon road bike (please note: other bike types available. Email us for details).

skill level


number partecipants

2-10 (please note: larger groups may be accommodated upon request)

minimum age

14 years old

fully guided


support vehicles

Yes, for rides with 4+ participants (*)

road type

All paved

(* please note, for mechanical issues or riders unable to finish the ride for groups of less than 4 riders, there is the possibility for a ride back to Gaiole, included in the tour price)


Imagine a perfect day on a full carbon Pinarello or Bianchi road bike, cycling on some of Italy’s most iconic roads, past vineyards, olive groves and cypress trees. Roads and panorama which have been immortalized in Giro d’Italia and in Strade Bianche by pro riders.

The Chianti Classico area is a perfect area for enjoying road cycling at its finest, this is why many pro riders are based in this area, as there is something for everyone: gradual climbs, hairpin turns, white knuckle descents, flats, grueling accents – in Chianti Classico there is a certain rythym to the road biking, here is your opportunity to be drawn to its captivating allure. You may never wish to leave again, just like us.

This ride allows you to explore the three most charming medieval wine villages in Chianti: Gaiole, Radda and Castellina. They constituted the “League of Chainti” in the Middle Ages and today are lovely tourist destinations related to fine wines.

The ride starts in Gaiole in Chianti, a quiet and very beautiful wine village, as well as home to the world famous vintage bike race called L’ Eroica.

We bike south towards Siena on the Chiantigiana road, then continue on a gradual, very scenic climb to Radda in Chianti surrounded by vineyards on all sides. Then, prepare your legs and mind for the steep 15% 1 KM ascent into the city centre of Radda. You will have earned your wings and the incredible 360 degree panorama from one of Tuscany’s most charming medieval wine villages, looking out onto the surrounding Chianti countryside.

Afterwards, we will give our legs a break, and unwind on a lovely ridge road connecting Radda to Castellina.

Then there is time for an optional stop for lunch (not included in the tour price) at the flagship winery restaurant or other nearby bars and trattoria located in downtown Castellina.

We will also enjoy a wine tasting at one of the area’s most prestigious wine estates, of their best wines and vintages.

Later on, we continue by bike, on a very long and memorable descent, and loop back around towards Radda once again.

The last leg of our journey retraces a small portion of L’Eroica vintage bike ride, climbing on a switchback filled road, through shady woods, on the way to Badia a Coltibuono. Then, a final 5 KM, exhilarating decent back to Gaiole in Chainti.

What an incredible road ride – Ride like a Tuscan!

Summary Price: 195€ for person

Ride like a Tuscan


Book this tour now


World class road cycling on some of Tuscany’s most beautiful roads. Ride roads immortalized by top pro cyclists in Strade Bianche and Giro d’Italia. Feel the heady excitement of riding a top full carbon Pinarello or Bianchi road bike in Chianti Classico. Enjoy wine tasting at one of Tuscany’s most prestigious wine estates.


  • Fully guided, private or private tour
  • Pinarello or Bianchi full carbon road bikes with Shimano Ultegra components
  • Tuscany Bicycle water bottle
  • English speaking, tour leader(s)
  • One wine tasting at a leading Chianti Classico estate
  • 50-70 KM total distance biked
  • Fully van supported (for rides with 4+ participants)

(please note, other bike types are available. e-mail us for details)