Tuscany - Val d’Orcia and Chianti

Ride the hills of quintessential Tuscany, explore Siena, and discover lesser-known villages.

This tour visits some of Tuscany’s iconic destinations and is filled with culture and authentic beauty. While Tuscany does not need any presentation, it never disappoints. The area south of Florence, between Siena and Val d’Orcia, will set the stage for our exploration by bike. Remember that you can ride as little or as much as you want, or take the day off altogether.

Tour Dates


  • June 4 – 10
  • September 11 – 17


  • Contact me for departure dates

Tour Details

  • Duration: 7-days
  • Ride Type: Road 
  • Difficulty: Active (2 of 3)
  • Average Daily Mileage: 20 – 50
  • Price: $4,995

We start in Cortona, the delightful hill town made famous by Frances Mayes in her bestselling novel, Under the Tuscan Sun.

We’ll then move to the countryside in the outskirts of Pienza. You will visit medieval hilltop towns, abbeys, and wineries.

Siena is the embodiment of a medieval city and it will be our grand finale. In the Chianti region, you will explore part of the production area with a visit to the Brolio winery (the “inventors” of Chianti). We should also mention that this area has been known since Roman times for its thermal springs and we will take advantage of that.

Val D’Orcia Natural and Cultural Park

The natural features of the valley, together with the cultural identity of the community that has lived there for centuries, make Val d’Orcia a unique area and for that reason it’s been designated a World Heritage site by UNESCO.

The municipalities of Val d’Orcia are:

  • Castiglione d’Orcia
  • Montalcino
  • Pienza
  • Radicofani
  • San Quirico d’Orcia

Tour Itinerary

DAY 1 – Transfer from Florence airport; Cortona – 10 mls – Hilly
DAY 2 – Lago Trasimeno – 33 mls – Rolling
DAY 3 – Val d’Orcia – Pienza – 30 mls – Hilly
DAY 4 – Val D’Orcia – Sant’Anna in Camprena –  31 mls – Hilly
DAY 5 – Chianti loop – 30 mls – Rolling hills
DAY 6 – Siena – 31 mls – Hilly
DAY 7 – Transfer to Florence airport, or your next Tuscan destination.

* Request the full itinerary via the contact form below.


  • Two important wine regions: Chianti and Montalcino-Brunello 
  • UNESCO World Heritage Sites of Val d’Orcia and Siena 
  • Villages of Pienza, Montepulciano, Montalcino   
  • Stunning cycling along rolling hills covered with vineyards and quaint medieval villages
  • The thermal spa of Rapolano Terme
  • Some of the best regional food in Italy     
  • Crete Senesi         
  • Cortona, the village featured in “Under the Tuscan Sun”   
  • Private wine tasting at Castello di Brolio


  • Two professional tour guides throughout the program
  • All accommodations in 4-star hotels (one 5-star)
  • All breakfasts, all lunches, and all dinners
  • Wine and beer with meals, coffee, cappuccino, and gelato stops
  • Tastings of wine and local specialties
  • Entrance to thermal spa
  • Logistical support during the tour and luggage transfer
  • Guided tour of Siena
  • Shuttle at the beginning and at the end of the tour
  • All activities mentioned in the day-by-day description
  • Bianchi bike rental 
  • GPS navigation and maps (digital)

Overall, you exceeded my expectations. I was so blown away by this trip. One of the best experiences I have had since doing these types of trips.

– Amanda B

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