Hiking Tour in Tuscany


Walking through the breathtaking landscape of the hills of southern Tuscany between romantic hill top towns is a magical experience. Your journey winds through a unique linear, almost geometric landscape of hills, vineyards and olive trees between renaissance towns and medieval monasteries. Walking through the lesser known wine regions south of Siena allows you to escape the pace of 21st century life and discover the tastes and textures of this beautiful region of Italy.

This suggested walking vacation begins at Cortona and then a visit to the medieval hill top town of Montepulciano, before continuing to the renaissance town of Pienza, a UNESCO world heritage site. The journey continues through the tranquil Tuscan landscape to a succession of architecturally and historically fascinating towns and monasteries while enjoying the generous Tuscan hospitality before your journey’s end in Siena.


  • DAY 1: Arrive Starting Point: Cortona
  • DAY 2: Montepulciano to Pienza - 9.5 miles
  • DAY 3: Pienza to Bagno Vignoni - 9.5 miles
  • DAY 4: Bagno Vignoni to Sant’Antimo - 8 miles
  • DAY 5: Montalcino to Buonconvento - 14 miles
  • DAY 6: Buonconvento to Monte Oliveto Maggiore - 6.5 miles
  • DAY 7: Buonconvento to Siena - 10 miles
  • DAY 8: Goodbye to continue your adventure

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DAY 1: Arrive Starting Point: Montepulciano

It is recommended flying to Rome, Florence or Pisa and then catch the train to Chiusi (Train 1h30, 2h30 and 1h50 respectively). From Chuisi you can take a local bus or taxi the short distance to Montepulciano (20mins) Overnight: Suggested Hotel, Montepulciano

DAY 2: Montepulciano to Pienza: Walk: 9.5 miles

Starting from the San Biagio church you follow a quiet dirt road to the charming village of Montichiello where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing to Pienza. Pienza is a UNESCO World Heritage site because of it’s unique renaissance architecture and town planning. Additionally it is well known for the production of pecorino cheese and truffles. Overnight: Suggested Hotel, Pienza.

DAY 3: Pienza to Bagno Vignoni: Walk: 9.5 miles

Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths complex at Bagno Vignoni is the perfect location to spend the afternoon relaxing. Overnight: Suggested Hotel, Bagno Vignoni.

DAY 4: Bagno Vignoni to Sant’Antimo: Walk: 8 miles

A hard but enjoyable day following dry riverbeds through a fairly wild environment brings you to St Antimo, an isolated abbey situated in a pastoral landscape. After exploring the abbey walk or take the local bus to the Medieval town of Montalacino. Overnight: Suggested Hotel, Montalcino.

DAY 5: Montalcino to Buonconvento: Walk: 14 miles

A fairly tough day walking in the famous Brunello wine region. You will pass tthrough vineyards and olive groves, then finally entering the beautiful Tuscan Landscape of the "Crete" and Buonconvento, where you will stay in a lovely agriturismo. Overnight: Suggested Hotel, Buonconvento

DAY 6: Buonconvento to San Quirico d’Orcia: Walk: 12 miles

En route to San Quirico d’Orcia you pass through Brunello vineyards there will the opportunity to visit a nice winery at Torrenieri. Cross the railway line and carry on through wineries and iconic landscapes to San Quirico, a delightful walled town. You have just completed this section of the Via Francigena and perhaps you would like to reward yourself with a glass of delicious chianti in the medieval town square.

DAY 7: Buonconvento to Siena: Walk: 10 miles

Today you should start with a short transfer from Pieve a Salti to Grancia di Cuna to start the walk to Siena. Walking through a landscape of rolling hills and small hamlets until you are rewarded with the view of Siena in the distance. Enter the town through Porto Romana, one of the medieval gates and walk thought the city to reach your hotel. Overnight: Suggested Hotel, Siena. 

DAY 8: Goodbye.

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Hiking Tour Hilltowns of Tuscany

Hiking Tour Hilltowns of Tuscany


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