Tuscany is art. Perfectly proportioned villas framed by elegant cypresses cap lines of hills. Towns and villages display layers of heritage in stately palazzi, decorated window frames, even doorknockers and wine bottle labels. Picture yourself walking in Tuscany, and imagine the delights of a self-guided tour.



Montepulciano, Province of Siena, Italy

Day 1


Pienza, Province of Siena, Italy

Day 2

Rocca d’Orcia

Rocca D'orcia, Province of Siena, Italy

Day 3


Montalcino, Province of Siena, Italy

Day 4


Buonconvento, Province of Siena, Italy

Day 5+6


Siena, Province of Siena, Italy

Day 7+8

What’s Included in the Cost of Your Trip?


7 nights hotels
All breakfasts and 2 dinners
Detailed route instructions and maps
Luggage transfers and necessary transfers during the tour
Comprehensive Tour Details with detailed pre-trip information
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 between April 1 and October 31
Custom trips also available and can start any date. Call or email for details.


8 days / 7 nights, with 6 days of walking


Montepulciano / Siena


10-24 km (6-15 miles) daily distance which will take 4-6 hours.


Moderate hills


Classic Accommodation: US $2,500
Single supplement: US $625

Luxe Accommodation: US $2,950
Single supplement: US $740

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 You start in Montepulciano. You can reach Montepulciano from Chiusi by Taxi which is 20km away. Airports convenient to Chiusi are at Rome and Florence. From Rome train travel to Chiusi takes between 1 and 1.5 hours. From Florence the trip takes approximately the same time, but may require a change in trains. Your confirmation package will provide additional planning information.


Day 1


Arrival to your first accommodation in Montepulciano. Spend some time strolling around this beautiful town, with its many Renaissance palazzi and churches.


Day 2


Walk to the beautiful church of San Biagio on the outskirts of town, then head into the countryside. Stop at the walled village of Montichiello for lunch or an espresso before making your way to Pienza, a small town once called “the pearl of the Renaissance”. Partly redesigned by Pope Pius II, Pienza boasts a splendid Renaissance Cathedral and the charming Palazzo Piccolomini. Sample pecorino, a local sheeps’ cheese.
Hiking Distance: 15 km, elevation gain 490 m.*


Day 3

Rocca d’Orcia

Continue through a beautiful region of rolling hills, oak woods, and charming villages. Pass through San Quirico d’Orcia (409 m), another walled city with an elegant 12th century church and Bagno Vignoni, a spa town which has central square that has a huge steaming pool of sulfurous water famed for its healing properties since Roman times. End the day in the tiny village of Rocca d’Orcia.
Hiking Distance: 21 km, elevation gain 685 m or 15 km, gain 415 m.*


Day 4


On this challenging day, you will walk along dry riverbeds to reach the isolated Abbazia de Sant’Antimo, with its magnificent Romanesque church which the locals like to say was founded by Charlemagne in the 8th century. There are 10 more km to go before you get to today’s destination, Montalcino, so you’ll be picked up at the abbey and driven the rest of the way.
Hiking Distance: 13 km, elevation gain 585 m.*


Day 5


Montalcino is renowned for its ruby-red Brunello wines, so you’ll spend much of the day strolling through vineyards as well as olive groves. Then you’ll enter the primeval landscape of the crete senesi , where shepherds tend the sheep whose milk is used to make pecorino cheese. Spend the night at a delightful agriturismo near Buonconvento.
Hiking Distance: 24 km, elevation gain 525 m or 18 km, gain 380 m.*


Day 6


Enjoy a leisurely day relaxing around the pool or follow a hilly path to the 14th-century Benedictine abbey of Monte Oliveto Maggiore, one of the most impressive abbeys in Italy. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. The walk back from the abbey takes 3 hours.
Hiking Distance: 10 km, elevation gain 255 m.* (beginning with a shuttle to Monte Oliveto Maggiore)


Day 7


Walk along a winding dirt road over hills and through oak woods. Pass buenconvento and Murlo, a tiny medieval borgo, the oldest settlement in the area. A ring of houses forms Murlo’s defensive walls. Visit the Museo Etrusco which commemorates the town’s Etruscan origins. You’ll be met in Murlo and transferred to Siena.
Hiking Distance: 16 km, elevation gain 285 m.*


Day 8

Enjoy the sights of Siena before your departure. Stroll through the Piazza del Campo and to the spectacular Duomo, one of the few full Gothic Cathedrals built south of the Alps.

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


Albergo Il Marzocco, Montepulciano

The 16th Century hotel has been run by the same family for over 100 years and is an ideal place for a peaceful relaxing stay with spacious and comfortable rooms.

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.

Cisterna Nel Borgo, Rocca D’orcia

This charming and cosy albergo has only three rooms decorated with tradition and taste. It also has one of the best restaurants in the region.

Giglio Hotel, Montalcino

This charming family-run hotel is in the heart of Montalcino, and boasts spectacular views over the Tuscan countryside. Alternate: La Locanda del Loggiato, Bagno Vignoni available (no sur-charge)

Fattoria Pieve A Salti, Buenconvento

A traditional agriturismo (country hotel) with a spa, horse riding and outdoor & indoor swimming pools. There is a traditional Tuscan restaurant on site, where organic food is served.

Palazzo di Vali, 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. The rooms feature high ceilings and the breakfast is superb.


Villa Poggiano, Montepulciano

Located 2.8 km outside Montepulicano, Villa Poggiano overlooks the gently sloping hills of the Orcia Valley, in the midst of a 15-acre park. The Villa dates back to the XVII century and was restored to its past splendour. It has a XIX century travertine stone swimming pool with statues and fountains. Today welcomes its guests in exclusive but familiar atmosphere, an ideal place that combines elegance, peace and privacy.

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 Relais Osteria Dell’Orcia, località Bagno Vignoni near Castiglione d’Orcia

This 4-star hotel located in the hamlet of Bagno Vignoni is comfortable and charming, with outdoor swimming pool. There is a fine restaurant with excellent wine cellar.

Hotel Vecchia Oliviera, Montalcino

The Vecchia Oliviera Hotel is a fascinating ancient olive-oil mill that has been carefully renovated. Both its location, at the entrance to Montalcino, and warm welcome make it a relaxing place to stay. Swimming pool. Hotel Dei Capitani is an alternate option (no sur-charge)

Fattoria Pieve A Salti, Buenconvento

A traditional agriturismo (country hotel) with a spa, horse riding and outdoor & indoor swimming pools. There is a traditional Tuscan restaurant on site, where organic food is served.

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.

Randonnee Tours offers cycling and hiking tours in Italy, Tuscany
Trip starting at
USD $2,500

Trip Reviews

October 27, 2022

“We really enjoyed the flexibility of walking options, easy to follow GPS route instruction app, great restaurant and attraction suggestions, excellent selection of scenic paths.”

December 16, 2021

“Even though we’ve been home a month, our memories are vivid and positive. So positive in fact, we are considering returning in the fall to see the same beautiful area in another season!!”

December 14, 2021

“…Great choices!!! The accommodations were lovely, clean and comfortable. My favorites were the B&B in Rocco d’Orcia, El Capitani in Montacino and the farm near Buono Vente. We especially enjoyed the agritourissimo. Good job! I found the area manager provided us with good service.
The walks were beautiful and challenging. The villages were quaint with excellent accommodations and the service was stellar. We loved Tuscany and wish to walk other areas of this great region. “

June 9, 2019

“The walks were beautiful and challenging. The villages were quaint with excellent accommodations and the service was stellar. We loved Tuscany and wish to walk other areas of this great region.”

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