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7 days
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Under the Tuscan Sun Trail, from Siena to Cortona - Italy
Nel cuore della Val d'Orcia da Siena a Cortona
7 days, price from
  € 819


“My idea of heaven still is to drive the gravel farm roads of Umbria and Tuscany, very pleasantly lost.” writes Frances Mayes in her book "Under the Tuscan Sun", which - together with the movie - enchanted and sparked the imagination of thousands of readers and viewers, a fictional portrait of the very real Tuscan landscape in its most iconic beauty. 

If you are among those readers, know that this trip will turn your dreams into reality: you will see all the fig trees, cypresses, soft rolling hills and hamlets you have ever dreamt of, and much more. Starting from Siena, with its "Contrade" and the shell-shaped square, this trail takes you through the thermal baths of Rapolano, prestigious wineries serving the divine local "Brunello" red, the lunar, iridescent landscape of the "Crete Senesi", dense oak woods and open pastures dotted with cypresses and "cascine". 

Last but not least - Cortona, where "Under the Tuscan Sun" was set: a beautifully located hilltop town, home to artists and Saints, Romans and Etruscans; the perfect place to end your quintessential Tuscan adventure in, ready to delve into your next literary adventure. 


Day 1   Arrive in Siena

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.


Day 2   From Siena to Vescona, transfer to Asciano 11.5 km

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.


Day 3   From Vescona to Asciano, 15.5 km

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.


Day 4   Walk from Asciano to Serre di Rapolano, 7/15 km

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.


Day 5   Walk from Serre di Rapolano to Sinalunga, 20km

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.


Day 6   Walk from Sinalunga to Farneta, 18km

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.


Day 7   Walk from Farneta to Cortona, 16km

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.


Day 8   Depart from Cortona!

Last day included. Tour ends after breakfast.

Practical info

The closest International Airports to get to Siena are: Florence “A. Vespucci” Airports Pisa //  and Rome

From the airports you can take a train and then busses to reach Siena.

It is possible to park the car at the first accommodation for the whole trip


What is included

What is not included

Optional Services

These services can be added to the ones included in the base price of the tour: