8 days/7 nights with at least 6 of days cycling

Start any date from April 15 to November 15.

We recommend to start this tour on a Thursday to see the market in Sinalunga held every Tuesday

Moderate/Challenging 20-40+ miles daily
1 day gently rolling
3 days are moderately rolling
2 days are hilly

Classic Accommodation:   US$1680    

Single Supplement:


Luxe Accommodation:
Single Supplement


Learn more about accommodation levels 

  • 7 nights hotels 
  • All breakfasts and 2 dinners
  • Luggage transfers
  • Use of a high quality performance hybrid or road bike and accessories
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  • Details with detailed pre-trip information
  • Detailed route instructions and map
  • Personal meet & greet with our local Area Manager
  • Area manager available on call throughout the tour
  • Access to Loyalty Program and other exclusive benefits

Our trip starts from Siena.

If coming via London, Air UK flies direct into Florence from Stanstead airport.

From Florence, the easiest way to reach Siena is via bus (it takes less than 1 hour).

If you are flying into Rome or Milan or Pisa, you can reach Siena by train. The journey from Rome takes about 3 hours.


Learn more about trip preparation

Randonnée Tours


Tuscany Cycling 8 Days
Enjoy la dolce vita! Tuscany is the classic Italian destination, and this adventure offers you famous sights and unusual discoveries. Travel at your own pace and take time to experience the best of Tuscan living. Explore winding walkways in Sienna and ride through hilltop villages in the heart of Chianti, San Gigminano, Castellina, Monterrigioni, Asciano, Pienza,and Montepulciano.


Tuscany Cycling 8 Days Day 1
Arrival in Siena. Siena is one of the most enchanting cities in Italy. Take some time to visit the medieval centre with majestic buildings, such as the palazzo Comunal on Il campo and a profusion of churches and small museums rich in artworks.

Day 2
Starting from Siena, cycle north through fields and vineyards, stopping in San Sano at a favorite restaurant for lunch. Afterwards, you can visit Radda on your way to Castellina.
Distance: 46 km, elevation gain 690 m.*

Day 3
Today choose between a route through the surrounding countryside with a visit to Castle Meleto or a route to San Gigminano, with its medieval towers evoking times past. Back in Castellina, opportunities are many for wine tasting at one of the enotecas in town. Your hotel in Castellina, formerly a palace is now a charming hotel with swimming pool and stunning common rooms.
Distance: 52 km, elevation gain 699 m or 62 km, gain 868 m.* 

Tuscany Cycling 8 Days Day 4
Your route today takes you to Monterrigioni; with its perfectly preserved walls and cobbled streets you will find the charm immediate. Your hotel, located in the country-side with pool and surrounded by an extensive park, may tempt you to relax. For those interested in cooking lessons prior to dinner, please call the office for details.
Distance: 64 km, elevation gain 576 m or 53 km, gain 693 m.* 

Day 5
This will be a favorite day of riding as you pedal through rolling countryside lined with cypress trees. Asciano is full of museums and monuments, and is also a perfect base to reach the Abbey of Monte Oliveto Maggiore, where monks still produce wine, honey, olive oil and a cure-all herb liquor. Art lovers will not want to miss the frescoes painted by Sodoma and Signorelli that have been preserved here since the 15th century. Your 3-star hotel in Asciano is brand new with swimming pool and gardens.
Distance: 43 km, elevation gain 541 m or 23 km, gain 255 m.* 

Day 6
Visit the tiny villages of Petroio and Castelmuzio on your way to Pienza, full of Renaissance monuments; your hotel here is quietly situated 150 meters from the central plaza and has large comfortable rooms and a casualness that you will enjoy (and a brand new pool in 2007).
Distance: 30 km, elevation gain 495 m.*

Day 7
On your final day or riding, you’ll ride to Montepulciano, riding through a ‘photographers’s paradise’. Montepulciano is the biggest and highest of Tuscany’s hill towns at 655 meters with medieval alleyways and lots of Renaissance palaces and churches.The surrounding countryside produces a wine called Vino Nobile di Montepulciano and has been doing so since the 8th century.
Distance: 37 km, elevation gain 485 m or 45 km, gain 651 m.*

Day 8
Departure day. Be sure to spend a final few moments enjoying the delights of Tuscany before you catch your train to your next destination.

*Distance and elevation gains may vary depending on hotels chosen for specific departure.

"We had a fabulous trip! The weather was perfect and the scenery never censed to be breathtaking. The bike routes were challenging in terms of hills but very pleasant because of the lack of traffic and the never-ending views. The accommodations were all good and got progressively better as we went. Same for the meals. It was an unforgettable trip."

- B. and M. Hole

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