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.

Location

Siena

Siena, Province of Siena, Italy

Day 1

Castellina-in-Chianti

Castellina-in-Chianti

Day 2+3

Siena

Siena, Province of Siena, Italy

Day 4

Asciano

Asciano, Province of Siena, Italy

Days 5

Pienza

Pienza, Province of Siena, Italy

Day 6

Montepulciano

Montepulciano, Province of Siena, Italy

Day 7

Montalcino

Montalcino, Province of Siena, Italy

Day 8+9+10

What’s Included in the Cost of Your Trip?

INCLUDED IN REGULAR TRIP

9 nights hotels
All breakfasts and 3 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

Not Included

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

Particulars

EVENT DATES

2019 & 2020
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.

TOTAL DAYS

10 days / 9 nights with 8 days of days cycling

ARRIVE / DEPART

Siena / Montalcino

ACTIVITY LEVEL

Moderate/Challenging: 20-40+ miles daily.

TERRAIN

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

COST

Classic Accommodation: US $2,160
Single Supplement: US $670

Luxe Accommodation: US $3,080
Single Supplement: US $1,010

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 or would like to confirm space on this trip before making your reservation, please contact us at info@randonneetours.com or by telephone at 604.730.1247.
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.

1

Day 1

Siena

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.

2

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.*

3

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.*

4

Day 4

Sovicille

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.* 

5

Day 5

Asciano

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.* 

6

Day 6

Pienza

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.*

7

Day 7

Montepulciano 

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.* 

8

Day 8

Montalcino

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.*

9

Day 9

Montalcino

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.* 

10

Day 10

Montalcino

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

Classic

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.


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 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.


Luxe

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, 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
Trips starting at
CAD $2,844.56

Tour Reviews

5.00 based on 3 reviews
November 15, 2019

ust got back from Nova Scotia and want to say that we had a fabulous trip. Thanks so much for doing your job so well. The routes were great and so were the accommodations.

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.”

December 4, 2018

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

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