10 days/9 nights with 8 days of 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
4 days are moderately rolling
3 days are hilly

Classic Accommodation:   US$2160  

Single Supplement:


Luxe Accommodation:
Single Supplement


Learn more about accommodation levels 

  • 9 nights hotels 
  • All breakfasts and 3 dinners
  • Luggage transfers
  • Use of a high quality performance hybrid or road bike and accessories
    Learn more
  • We require that you bring your own helmet for safety and hygiene reasons
  • 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.  Your trip finishes in Montalcino You can take a taxi from Montalcino to Chiusi which take about 1 hour and cost
around 80 Euros. There are train departures from Chiusi throughout the day from Florence or Roma. Travel time is approximately 2 hours.


Learn more about trip preparation



Randonnée Tours


Tuscany Cycling 10 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 Siena and ride through hilltop villages in the heart of Chianti, San Gigminano, Castellina, Monterrigioni, Asciano, Pienza, Montepulciano and Montalcino.


Hotel Il Giardino

Palazzo di Valli, Siena

This charming 3-star hotel is a favourite in Sienna. Boasting a beautiful view over the countryside and a 10 minute walk to the historical center, its location is also ideal for cycling out of town on Day 2. The rooms feature high ceilings and the breakfast is superb.


Palazzo Squarcialupi
Il Colombaio, Castellina in Chianti
This charming hotel has comfortable rooms, and a lovely swimming pool. Located close enough to walk (150 m) to restaurants in Castellina-in-Chianti.
Villa Cennina Hotel Le Valline, Sovicille

Located among the hills of the Crete Senesi and the Val di Merse, this hotel boasts outstanding views in every direction, a large swimming pool and a tranquil setting. There is a restaurant catering to guests on site.


Hotel La Pace
Hotel Podere Alberese, Asciano

This property is our newest discovery; this family-owned 17th century property is surrounded by vineyards (the family makes outstanding wines), olive trees and organic gardens. There is a heated swimming pool to enjoy on the property. There isn’t a restaurant on the property but there are two good options, one right next door and another 900m distant.


Hotel San Gregorio Hotel San Gregorio, Pienza
This 3-star hotel has very large rooms and swimming pool and is conveniently located steps to the historical district of Pienza. Breakfast is served in an adjoining restaurant.

Hotel Vecchia Oliviera, Montalcino

The Vecchia Oliviera Hotel is a fascinating ancient olive-oil mill that has been carefully renovated. Both its location and warm service make it a relaxing place to stay. Swimming pool.

Hotel Santa Caterina

Hotel Santa Caterina, Siena
This 18th century villa has been converted into a cozy hotel. Guest rooms overlook the valley. It is steps away from the medieval city gates with lots of restaurants to choose from.

Palazzo Squarcialupi, Castellina in Chianti

This palazzo boasts a superb location, right in the historic center of village, largue sumptuous lounges and bar, and a large outdoor swimming pool.

Relais Borgo di Toiano, Sovicille

This 4-Star Tuscan villa boasts panoramic views over vineyards, with a pleasant swimming pool in a very quiet setting. There is a small bar serving light food; good restaurants can be reached 1 km distant.


Hotel Borgo Casa Bianca, Asciano

This eighteen-century property is one of the most magnificent 4-star hotels in Tuscany. There is a large swimming pool, a hydro-massage bath tub, and tennis-courts, all surrounded by an amazing landscape and a good restaurant on site.


Hotel Il Chiostro Hotel Il Chiostro, Pienza
Formerly a Franciscan convent, this 4-star charming hotel boasts comfortable rooms, outdoor swimming pool and a fine restaurant with terrace overlooking the stunning Val d'Orcia valley.

Hotel Il Giglio, Montalcino

This charming hotel is Montalcino's best - family run, on a quiet street in the historic centre. "...the best part is the view of the cliff-clinging houses of Montalcino to your left and the rumpled patchwork of green valleys stretching out below." - Lonley Planet

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