8 days/ 7 nights, with 6 days of walking

Start any date between April 1 and October 31

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

Classic Accommodation:   US$1570

Single supplement:



Luxe Accommodation:   US$1930

Single supplement:



Learn more about accommodation levels  

  • 7 nights hotels
  • All breakfasts and 2 dinners
  • Detailed route instructions and map
  • Luggage transfers and necessary transfers during the tour.
  • Comprehensive Tour 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

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 and requires no change. From Florence the trip takes
approximately the same time, but might require a change in trains.

Your confirmation package will provide information on getting to Montepulciano.


Learn more about trip preparation




Randonnée Tours



Tuscany Walking 8 days

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.


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.

Il 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.

Hotel Il Chiostro

Via 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 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 Chiostro 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 *Classic Inn

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

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.

"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."

- M. Klug

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