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

Tour Operator n° – 41650

Chianti villages north – road cycling

starting point

Tuscany bicycle, Gaiole in Chianti


210 per person

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


7-8 hours

elevation gain

1600 mt

distance biked

90 km


Chianti classico 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 by request)

minimum age

16 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)


This is the  blockbuster follow up to our original, bestselling Chianti Villages West  – Road Cycling itinerary. You asked for more miles, more elevation gain, more thrilling downhills and grueling uphills – and Chianti Villages North is our answer to the letters and emails we received.

Imagine a challenging, long and exhilarating ride, for serious road cyclists only, hitting all the “must sees” in Chianti Classico, riding a state of the art Pinarello Gan full carbon bike directly derived from the Pinarello Dogma F8, during a full day immersion by bike in the heart of Tuscan wine country.

This ride begins in Gaiole in Chianti, where our store is and continues west to Radda in Chianti, where a leg pounding 15% ramp of 1 KM awaits you, to reach the historical centre of Radda. Afterwards you enjoy a small respite and easy rollers on the way via a scenic ridge road to Castellina in Chianti.

Castellina is a beautiful medieval wine village and perfect for an espresso stop, at one of its many charming outdoor caffès. Afterwards, your efforts up until now are handsomely rewarded with a thrilling decent towards San Donato in Poggio on one of the area’s most beautiful roads with sweeping curves downhill and pristine tarmac.

We will stop en route at a boutique, world class winery to enjoy a winetasting or if you prefer at one of the area’s leading artisanal gelato producers to sample their award winning gelato creations. There will also be time during the ride for lunch, and we are happy to make recommendations based upon what you are looking for (please note, lunch is not included in the tour price).

From San Donato, the route will make its way towards Greve in Chianti, and include two of the area’s most iconic climbs – Quattro Strade and Passo dei Pecorai. Greve is Chianti Classico’s largest village, with a lovely trapezoid shaped piazza, dotted with local eateries, butcher shops and bars. From Greve, there is a gorgeous, gradual climb into Panzano featuring an obligatory visit to Dario Cecchini’s world famous butcher shop, where AC/DC is often playing in the background, intermingled with Dario’s recital of Dante’s Inferno whilst preparing meat cuts.

Afterwards another incredibly scenic decent out of Panzano, sweeping past the Conca d’Oro (Golden Slopes) of Chianti, where some of the best Chianti Classico wines are produced – then a long false flat heading in the direction of Badia a Coltibuono – a Vallobrosian monastery now home to a world class organic winery of the same name, famed cooking school and flagship winery restaurant.

From Badia, the last incredibly gorgeous decent full of tight, hair pin turns leading us back to Gaiole in Chianti. What a day and what an amazing ride – Ride like a Tuscan!

Summary Price: 210€ 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
  • 90 KM total distance biked
  • Fully van supported (for rides with 4+ participants)

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