I sapori della Toscana

Cycling in Tuscany, savor the most famous foods and wines while biking around the most enchanting routes of Tuscany

Bicycle in Tuscany to discover the most scenic routes of Chianti biking along gentle hills and vineyards, discover the outstanding panoramas of Val d’Orcia with Montalcino (home of Brunello wine), Pienza and San Quirico. After a couple of days of cycling, one rest day to explore the area more in depth and learn more about the Brunello di Montalcino wine region, the king of red wines! The day after jump again on the seat and keep cycling in Tuscany all the way down to the Tuscan coastline (called Etruscan Riviera) then ride up again through Volterra along quite countryside roads, imposing castles located on hilltops, bike through charming medieval villages and refresh yourself at the ancient fountains of the parishes.


  • Explore the sweetets hearth of Tuscany at your own pace.
  • Tour guides are former professional cyclists.
  • Visit UNESCO sites like Orcia River Valley, Siena, San Gimignano.
  • Bike through the most famous wine regions in the world like Chianti and Brunello.
  • Outstanding foods and wines.
  • 5 days – Approx 450 km – Ascent 4500 m. – Descent 4500 m. – OUR ACTIVITY LEVEL GUIDE
  • Supporting van.

Feel free always to enquire a further customization of the tours, according to your physical conditions, your desires or experience.

Day 1 – Bike from the very hearth of the Tuscan hills towards the two gems of the medieval Tuscany: San Gimignano and Siena. San Gimignano (the medieval Manhattan) among olive groves and vineyards. Siena is simply amazing, with Piazza del Campo (where the Palio horse race takes place) and its Duomo built in white marble.

Day 2 – This Tuscany bike tour stretches entirely in a World heritage site: the Orcia River valley. The entire valley is UNESCO site due to the perfect preservation of the landscape and of the villages located there like Pienza and San Quirico.

Day 3 – Day off. Explore the region of Brunello di Montacino wines or just relax by the pool.

Day 4 – Tuscany bike tour, start cycling from Buonconvento to the Etruscan Riviera a pretty wine region located south of Leghorn and famous for its wines called Super Tuscans. After some very scenic climbs arrive in Massa Marittima, a beautiful town on the mountain side facing the sea, beautiful colors, nice ambiance and good food.

Day 5 – The cycling starts in flat up along the coast between the sea and the wine hills of Bolgheri, home of famous wines like Sassicaia and Ornellaia. Then turn towards the mountains of Volterra famous since the ancient time for their salt mines and alabaster quarries. Afterwards keep riding until the starting point.

Price per person € 860,00 calculated on a base of 10 participants.

If your party is smaller or bigger, we will send you a customized quotation.


  • Private tour with your own bicycle
  • Minimum #1 maximum #15 participants (advised)
  • 4 nights in bike hotels in half board treatment.
  • Mechanical assistance
  • Support van with driver for the whole tour.
  • Former professional cyclist as your tour guide.
  • Light lunches and food and wine tasting en route

NOTICE: the prices are subjected to reconfirmation, because hotel rates may change according to the period of the bike tour.


  • Rental bikes: available road bikes, mountains bikes, e-bikes
  • Car/coach transfer
  • Tips
  • Other extras not listed above

Tour details

  • Starting point Castelfalfi. Other meeting point on request.
  • Duration: 5 days
  • Total length: approx. 450 km
  • Total elevation gain: 4200 mt.
  • Type of road: paved
  • Activity Level: from intermediate to strenuous.
  • Advised clothing: cycling garment with mandatory helmet. Otherwise: T-shirt-Sweater-Wind-breaker-Sneakers-Sunscreen-Sunglasses

Need more customization?
Send us your requests!

Are you a larger group?

Wish to modify the itinerary?

Wish to add or cut some stages?

Need car/coach transfers?

Wish to have more rest days?