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. From Florence the trip takes approximately the same time, but may require a change in trains.

Your confirmation package will provide additional planning information.


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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.


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.
Distance: 15 km, elevation gain 490 m.*

Day 3
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 cillage of Rocca d’Orcia.
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.
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.
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.

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.
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.

"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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