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
    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.


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.

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

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 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 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.


"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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