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.

STRAIGHT TALK: We highly recommend the Luxe trip as the hotels are lovely, unpretentious and ideally situated for the best cycling routes and in or near the best villages. In Siena, the 5-star Grand Hotel Continental is an upgrade option for your first night’s stay.



Siena, Province of Siena, Italy

Day 1



Day 2+3


Siena, Province of Siena, Italy

Day 4


Asciano, Province of Siena, Italy

Days 5


Pienza, Province of Siena, Italy

Day 6


Montepulciano, Province of Siena, Italy

Day 7


Montalcino, Province of Siena, Italy

Day 8+9+10

What’s Included in the Cost of Your Trip?


9 nights hotels
All breakfasts and 2 dinners
Luggage transfers
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

Not Included

We require that you bring your own helmet for safety and hygiene reasons



Start any date from April 15 to November 15
Custom trips also available and can start any day. Call or email for details.
Custom trips also available and can start any date. Call or email for details.


10 days / 9 nights with 8 days of days cycling


Siena / Montalcino


Moderate/Challenging: 20-40+ miles daily.


1 day gently rolling, 4 days are moderately rolling & 3 days are hilly


Classic Accommodation: US $2,950
Single Supplement: US $740

Luxe Accommodation: US $3,450
Single Supplement: US $865

Bike Rentals

Hybrid or Racing Bikes: US$400

E-Bikes: US$720

E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.  

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.  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.


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

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.
Ride Distance: 46 km, elevation gain 690 m.*


Day 3

Castellina in Chianti

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.
Ride Distance: 52 km, elevation gain 699 m or 62 km, gain 868 m.*


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.
Ride Distance: 64 km, elevation gain 576 m or53 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.
Ride Distance: 43 km, elevation gain 541 m or 23 km, gain 255 m.* 


Day 6


Following quite rolling roads south, you’ll 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).
Ride Distance: 30 km, elevation gain 495 m.*


Day 7


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. We’ll recommend local enotecas where you can taste.
Ride Distance: 37 km, elevation gain 485 m or 45 km, gain 651 m.* 


Day 8


Ride through a classic Tuscan tableau of cypress trees, pines and olive groves to the ancient village of Bagno Vignoni; see a Roman bath favored by members of the Medici family. Continue to Montalcino, a picturesque town famous for Brunello wines and medieval architecture.
Ride Distance: 45 km, elevation gain 750 m.*


Day 9


On this day loop from Montalcino, you will cycle to Buonconvento, a picturesque 14th Century medieval village and to the Bibbiano fortress that overlooks the Ombrone Valley.
Ride Distance: 48 km, elevation gain 532 m or 24 km, gain 182 m.* 


Day 10


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


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 900m distant.

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, 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. Note; 5-star Grand Hotel Continental Siena is an upgrade option in Siena. From US$150pp upgrade.

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, 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

Randonnee tours offers cycling and hiking trips in Italy
Randonnee Tours offers cycling and hiking tours in Italy, Tuscany
Tuscany, Italy
Trip starting at
USD $2,950

Trip Reviews

October 31, 2023

“One of the best we have done, including those with you and with others. Bikes were excellent, and very well maintained. Great routes, good accommodation, fabulous scenery and people.”

December 16, 2021

“I just wanted Randonnée Tours to know that my brother and I really, really enjoyed our self-guided bicycle tours through Tuscany and Umbria, Italy it was one of the best, most relaxing vacations I have ever taken. I felt I received real value for the money paid.”

December 16, 2021

“Area managers were gracious and helpful.”

December 14, 2021

“Pre-trip information was very impressive and complete, and some of the material would be very helpful to the first-time traveler to Europe. The bicycles were very nice and obviously new; they worked flawlessly. We booked Classic accommodations, and we could not have been more pleased. All accommodations met or exceeded expectations. All hosts were gracious and helpful, and all added to the pleasure of the tour.”

December 14, 2021

“We are big fans of your area manager, at all times he went well beyond what we expected and did everything he could to make certain that we had a great trip, which we did.
Our experiences with you have been great and in booking our next tour (we are already talking about next year) you will be at the top of the list.”

June 9, 2019

“We had a fabulous trip! The weather was perfect, and the scenery never ceased to be breathtaking. All the accommodations were great, Castello, di Velona, was spectacular. Same for the meals. Pienza was my favorite town. The locations were a nice combination of towns and country and more specifically a combination of villas, farmhouses, palaces, and the castle. The bike routes were challenging in terms of hills but very pleasant because of the lack of traffic and the never-ending views. It was an unforgettable trip.”

December 4, 2018

“Loved Tuscany. Some beautiful hotels. Great group of friends. Just some lovely memories.”

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