We Bike Tuscany

Recommended in
Lonely Planet Florence &
Tuscany travel guides
Tuscan Valleys


Bike through a patchwork of rolling vineyards and olive groves surrounded by ancient hill towns. Taste satiny olive oil, full bodied Nobile di Montepulciano wine and sharp pecorino cheese. Swim in the natural hot water pools of Bagno Vignoni. All of this while cycling through Val di Chiana and Val d'Orcia, the most enchanting valleys of Tuscany.

From Cortona to Pienza, from Pienza to Bagno Vignoni, our itinerary heads into the valleys and through the hamlets of an untouched land. Here you will find a perfect, essential landscape of bare hills, and lone cypresses which, in ordered rows, will follow the progression of our route from the first to the last day.


$3260 per person

  • Duration: 5 days/4 nights
  • Distance traveled: 16 - 35 miles per day
  • Area: Tuscany
  • Nearest city: Arezzo, Siena
  • Places visited: Tuscany, Italy
  • Tour type: Road touring
  • Skill level: Intermediate
  • Season: April - October
  • Number of participants: 2-7
  • Minimum age: 16
  • Fully guided: yes
  • Support vehicles: yes
  • Transportation to start site: yes


Day 1 & 2

From Florence we transfer to Cortona (the famous setting of Under the Tuscan Sun, among many other things!). You enter the fortified walls of this ancient hill-top town passing under the massive keystone of the 8th Century B.C. Etruscan gate. Enjoy your rides with expansive views over the Chiana valley and, on DAY 2, a private tasting of Vino Nobile di Montepulciano after touring one of the most renowned wineries of the area.

Accommodation: 2 nights at Villa Baldelli (or Villa di Piazzano +$150 per person)

Day 3 & 4

We bike through the Chiana Valley to the starkly beautiful lunar landscape of the Orcia Valley. You'll see the land slowly change, turning from green to ochre before arriving at the Renaissance town of Pienza, our final destination. The following day we pedal into the wide open landscape of the Crete Senesi, past ancient hilltop towns, stone farmhouses, lone cypresses and lush vineyards. A pecorino cheese tasting is included in our route.

Accommodation: 2 Nights at Il Chiostro di Pienza

Day 5

A more relaxing ride today will take us to the medieval thermal village of Bagno Vignoni. The ride starts with an exhilarating 8 mile downhill in the very heart of the Val d'Orcia and ends with a relaxing soak in the thermal water pool of Bagno Vignoni. A well-deserved reward as our biking adventure in one of the the most scenic parts of Tuscany comes to a close.


  • Pick up/drop off in Florence or surroundings
  • Accommodations at the best Tuscan villas and inns of the region, all with pools
  • All breakfasts, cold drinks and snacks along the way
  • Three dinners with unrestricted menus, one free night for dinner on your own
  • Guided tour and tasting at winery; pecorino cheese tasting
  • One picnic lunch
  • Maps and detailed route directions
  • Van support and baggage transfers
  • 27-speed high-quality hybrid bikes, helmets, water bottles and handlebar bags
  • Small groups for personalized service


Please send us an email if you need more info. We will reply within 48 hours.