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

Tour Operator n° – 41650

Castle ride

starting point

Tuscany Bicycle, Giaole in Chianti


95 per person

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


3-4 hours

elevation gain

360 mt

distance biked

20 - 30 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)


A relaxing and enjoyable bike ride in the area of Chianti Classico. This itinerary is designed for more laidback bikers and families. It features some of the most beautiful backroads in Tuscany, with lovely views and endless photo opportunities.

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.

We will bike or walk up to the actual castle to enjoy the stunning views the castle has to offer, and its impressive walls.

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.

Then we will continue our ride on a gorgeous ridge road, through vineyards and past other castles, eventually looping back to Gaiole.

Summary price: 95 € for person

Ride like a Tuscan!


Book this tour now


Enjoy biking in Chianti Classico, on quiet backroads line with cypress trees. Savour wine tasting at one of Italy’s most prestigious 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)
  • Winetasting of best wines/vintages at one Italy’s top wine estates
  • 20-27 KM total distance biked
  • fully van supported (for rides with 4+ participants)

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