Arrive in Siena and check-in at the hotel. If you arrive early, enjoy a visit to the city, famous for its biannual “Palio” horse race, held in the most beautiful shell-shaped square in Europe: the Piazza del Campo. Don’t miss a visit to the Duomo, an architectural treasure, and numerous imposing medieval palaces. History comes alive as you meander through the narrow streets of this fantastically preserved jewel of Italy.

After a short train ride you start a long walk through the heart of Crete Senesi. You can enjoy great wiews of the iconic tuscan rolling hills landscapes enriched by old stone houses and lined cypresses. You pass through the famous "Biancane di Leonina" the "Sito Transitorio". The route to Vescona winds through gullies and cultivated fields, where we won't encounter much shade and the soil is mainly clayey. We reach the small village of Macigliani, perched on a spectacular balcony facing Siena.

Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. We continue our journey through the Crete Senesi until we join the Eroica. Following this legendary route we reach Asciano, the heart of the Via Lauretana.

It's an easy walk along the heart of Crete Senesi. You can enjoy great wiews of the iconic tuscan rolling hills landscapes enriched by old stone houses and lined cypresses. In case of rain some part can be muddy and slippery because the clay soil.

The thermal baths complex at Rapolano Is the perfect location to spend the afternoon soaking up the Tuscan warmth. Hop back on the road to walk the last few kilometres to your final destination of today, Serre di Rapolano.

It's a long walk through the tuscan countryside in a hilly landscape composed by woods, vineyards, olive groves and fields. Along the trail you can enjoy astonishing views of Valdichiana (the valley of Chiana River). Leaving Serre di Rapolano, we have the opportunity to look out and admire the landscape shaped by the travertine quarries. We then leave the Crete Senesi and enter the oak woods that separate us from Sinalunga. After admiring San Gimignanello from afar, we pass through the medieval village of Scrofiano.

Today you will walk along country roads, through the fields, and the canals banks digged in the past to drain the valley for the reclamation of lands. At half way you can make a short detour to visit the centre of Bettolle. At the end of the walk it is recommended to visit the Abbazia di Farneta which is just in front of the hotel.

It's a long but gentle walk through the planes and hills of Valdichiana. From here on, the path coincides with the Via Romea Germanica, for which we find the signposts. We continue along a flat and not very shady path that winds through small hamlets. When we reach the ancient parish church of San Michele, we begin to climb up to Cortona, the final destination of our journey.

You can avoid the ascent taking the alternative route to Camucia Cortona train station from where you can take the bus to Cortona.

Last day included. Tour ends after breakfast.