Day 1: Arrival in Siena
Arrival in Siena and visit the city, home to the famous Piazza del Campo and the impressive Duomo. Meeting with the guide and dinner in a local restaurant. Overnight stay in Hotel *** in Siena. 

Day 2: Buonconvento - Monteoliveto (4hrs 30min hiking, + 370m – 120m)
After a private transfer to Buonconvento, the journey starts with some trekking among the famous "Crete Senesi" (Clays) to reach the Abbey of Monte Oliveto, where you can visit the cloister with its renowned frescos. Along the rest of the route you will see the castle of Monterongriffoli's and the tiny village of Chiusure. Private transfer to Buonconvento. Dinner and overnight stay in hotel*** in Buonconvento.

Day 3: Buonconvento to Montalcino (5hrs hiking, + 480m – 120m).
Today we trek through the wonderful hills covered in the famous Brunello vineyards and pass by some spectacular private villas and cellars. In Montalcino, after tasting a glass of excellent wine, you can visit the Priori's Palace, the Loggia, the church of Sant' Egidio's and the Rocca, a pentagonal defence fortress built up in 1361 and forerunner of the Tuscan fortresses of the Medicean Age. Back to Buonconvento via public bus. Dinner and overnight stay in hotel*** in Buonconvento.

Day 4: Sant'Antimo - San Quirico d'Orcia (5hrs hiking, +540m – 460m)
Private transfer to Sant'Antimo (30min). From S. Antimo, definitely one of the most suggestive Benedictine Abbeys in the whole of Tuscany, presumed to be founded by king Charles the Great, we cross the Crete region enjoying a magnificent view, and then reach the castle of Ripa d'Orcia, from where you'll see the amazing panorama above the Orcia river, Castiglione and Rocca D' Orcia. We finish in Bagno Vignoni, a thermal resort since the Middle Ages, characterized by the stunning thermal bath right in the centre of the village, then pass by Vignoni, a little village with a medieval atmosphere, to reach San Quirico D'Orcia. Public bus to Montepulciano. Dinner and overnight stay in hotel*** in Montepulciano.

Day 5: Montepulciano - Pienza (4hrs hiking, + 350m – 200m)
Pienza, rebuilt in the mid-1400s by Pope Pius II and intended as his temporary residence, is the ideal Renaissance town. Monticchiello is a charming medieval village fairly well preserved throughout the centuries. You can discover it by losing yourself in its streets, stunning houses made of stones, little squares and towers. Montepulciano, the biggest town of the Chiana Valley with its famous "vino Nobile" that you just have to taste in the 15th century cellars in the old city centre. The town is an architectural jewel with its magnificent Renaissance palaces, narrow streets and brick buildings. Public bus to Montepulciano (20min). Dinner and overnight stay in hotel*** in Montepulciano.

Day 6: Pienza - San Quirico d'Orcia (3hrs 30min hiking, + 200m – 250m)
Public bus transfer to Pienza (20min). From Pienza we cross the typical "Crete Senesi" landscape, heading up and down of the hills, before reaching S. Quirico d'Orcia, located on the Via Francigena, an ancient path crossed by pilgrims on their way to Rome and which also contributed to the considerable economic growth of the town. Transfer to Montepulciano by public bus. Dinner and overnight in the hotel*** Montepulciano. Dinner is not included. Meals

Day 7: Montepulciano
A gentle walk in the area of the famous "Vino Nobile" wine. After a light lunch in the city centre, end of services and individual departure. Short transfer to the main bus station to take a bus to Siena, Florence or Pisa.