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.



Siena, Province of Siena, Italy

Day 1



Day 2+3


Sovicille, Province of Siena, Italy

Day 4


Asciano, Province of Siena, Italy

Days 5


Pienza, Province of Siena, Italy

Day 6+8


Montepulciano, Province of Siena, Italy

Day 7

What’s Included in the Cost of Your Trip?


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



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.
Custom trips also available and can start any date. Call or email for details.


8 days / 7 nights with at 6 days of cycling


Siena / Pienza


Moderate+ with challenging options


Most of the hill grades average 4-5%. You can do it.


Classic Accommodation : US $1,750
Single Supplement: US $450

Luxe Accommodation : US $2,450
Single Supplement : US $625

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. If you have any questions, please contact us.
Getting There 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.


Day 1


Arrival in Siena, 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 Piazza del Campo and a profusion of churches and small museums rich in artworks. This trip includes a 1-2 hour walking tour with a local guide whose knowledge of the history of this region will astound you.


Day 2

Castellina in Chianti

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. An add-on option takes you past Castello di Brolio, which has belonged to the Ricasoli family for nearly 800 years. Just opposite is a cool cafe with memorabilia from the L’Eroica bike race which is held each fall on some of these same roads.
Ride Distance: 46 km, 900 m or 75 km; 1335 m gain.* 


Day 3

Castellina in Chianti

Today choose between routes through the surrounding countryside with a visit to Castle Meleto and then time in Gaoile in Chianti. 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.
Ride Distance: 49 km, elevation gain 850 m or 62 km, gain 1055 m or 66 km; 1250 m.*


Day 4


Begin the day with a long descent to the valley before reaching Monterrigioni; with its perfectly preserved walls and cobbled streets you will find the charm immediate and an ideal place to enjoy morning coffee to fuel your climb to lunch at a local trattoria. There are add-on options that include one to San Gigminano, encircled by 13th-century walls and towers that, together with its hilltop setting make it compelling to visit. The hotel today is located in the country-side with pool and surrounded by gardens and vineyards will be a welcome treat. You can walk to dinner nearby. Ride Distance: 56 km; 700 m or 95 km; 1450 m or 110 km; 1630 *


Day 5


This will be a favorite day of riding as you pedal through rolling countryside lined with cypress trees and beautiful vistas. 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. We stay just east of Asciano in a property with an idyllic setting and swimming pool. Ride Distance: 56 km; 930 m gain or 78 km; 1365 m gain.


Day 6


Visit the tiny and utterly charming villages of Petroio and Castelmuzio and then stop to visit the monastery of Santa Anna, where the English Patient was filmed. An add-on option takes you to Montisi, yet another exceptional medieval hilltop village with tempting cafes. Arrive to Pienza, perhaps the most perfect hill-hill town in all of Tuscany. Treat yourself by staying at Il Chiostro, a former convent, now a 4-star hotel located in the very center of town and boasting pleasant gardens and pool. The restaurant options are many and we’ll recommend our favourites. Ride Distance: 32 km, elevation gain 700 m or 50 km; 1065 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 (and a wonderful wine tasting enoteca, we will share with you).The surrounding countryside produces a wine called Vino Nobile di Montepulciano and has been doing so since the 8th century. After a corkscrew descent down a dreamy road, enjoy lunch in the village of Monticchiello. There are add-on options, but most return to Pienza in time to enjoy the afternoon there.
Ride Distance: 37 km, elevation gain 740 m or 82 km, gain 1530 m.*


Day 8

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

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


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.

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.

Casale Il Colombaio di Toiano, Sovicille

This property is from the 1300s and beautifully restored with lovely and congenial hosts, Giuseppina and Paolo. The rooms are comfortable and the gardens sublime.

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 900 m away.

Hotel San Gregorio, Pienza

This 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, 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 a short stroll way.

Palazzo Squaricialupi, Castellina in Chianti

This palazzo boasts a superb location, right in the historic center of Castellina, with spacious lounges and bar, and a large outdoor swimming pool. Friendly and professional management.

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. Breakfast is served on the terrace overlooking the
rolling valley.

Hotel Borgo Casabianca, Asciano

This 18th 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 amazing landscapes. There is a great restaurant on site.

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.

Randonnee tours offers cycling and hiking trips in Italy
Randonnee Tours offers cycling and hiking tours in Italy, Tuscany
Trip starting at
USD $1,750

Trip Reviews

May 8, 2021

“Our overall experience was fantastic. Rossario is a fabulous area manager and felt we were in good hands should something come up…fortunately all went well. Bikes, accommodation, directions with lunch stop options – great. Will highly recommend to friends and will forward photos soon as would love to be able to do another tour 😉 Thanks again to Randonnée for making our trip fantastico !!!!!!!!!!”

June 9, 2019

“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.”

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