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

Tour Operator n° – 41650

Chianti wine and bike

starting point

Tuscany bicycle, Gaiole in Chianti


160 per person

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


6-7 hours

elevation gain

525 mt

distance biked

22 km


Chianti classico wine region of Tuscany

type tour

Road touring

bike type

Hybrid (please note: other bike types available for a nominal fee. Email us for details).

skill level


number participants

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

mostly paved, with optional unpaved, small section near the castle

(* 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)


An amazing bike ride in the area of Chianti Classico. This is an unforgettable journey on two wheels on very quiet backroads, past gorgeous vineyards and olive groves in the heart of Chianti Classico wine country.
There are a few gradual climbs along the way – greatly rewarded with amazing panorama – some of the best in Chianti.
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 to a gorgeous 11th century castle, one of the largest and best maintained fortified castles in the Chianti area. This castle was the birthplace for Chianti Classico wines in the late 1800’s.
The entrance fee to visit the majestic castle’s formal gardens is included in the tour price. Here, you will experience one of the most breathtaking views possible in Tuscany, from the fortified walls of the castle, admiring the formal gardens of the estate, featuring sweeping 360 degree views of vineyards all the way to Siena.
Afterwards, we will taste the best wines and vintages from this prestigious estate, which is has been in the same noble family for over 35 generations.
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.
Later on, we continue by bike to one of the area’s most beautiful medieval fortified villages, perched atop a very panoramic ridge. There will be lots of time for photo taking and enjoying the moment. The route features a challenging climb, but the vistas at the top make it well worth it.
Our efforts are rewarded by a cellar visit located in a medieval fortress dating back to the 13 C followed by a generous wine tasting of the best wines and vintages in this boutique winery’s designer tasting room with jaw dropping panorama.
After the tasting, riders may opt to hop in the support van or continue biking on a very gentle, fun and incredibly scenic downhill back to Gaiole.

Summary price: 160 € for person

Ride like a Tuscan!


Book this tour now


Enjoy biking in Chianti Classico’s most beautiful and low traffic area. Savour wine tasting at two of Italy’s top wine estates. Pedal on beautiful, state of the art Italian bikes. Soak in the history and magic of lovely castles and centuries old villages. Relish the company of your local, expert bike guide. Experience the beauty of the Chianti countryside, with lots of time to take photos.


  • Fully guided, private or private tour
  • High quality hybrid rental bikes
  • Helmets and Tuscany Bicycle water bottle
  • English speaking, tour leader(s)
  • One cellar visit in a medieval fortress, two full wine tastings at top estates in Chianti Classico
  • Entrance fee to the formal gardens of the castle
  • 20 KM total distance bikes
  • Fully van supported (for rides with 4+ participants)

(please note, other bike types are available at a nominal extra charge)