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Via Lauretana Toscana, Under the Tuscan Sun
Via Lauretana Toscana, Under the Tuscan Sun
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Duration :
7 days
Apr May Jun Jul Aug Sep Oct
price from € 819
Via Lauretana Toscana, Under the Tuscan Sun

Via Lauretana Toscana, Under the Tuscan Sun

Via Lauretana Toscana, Under the Tuscan Sun - 7 days

Via Lauretana Toscana, Under the Tuscan Sun - 7 days


“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
Day 2: From Vescona to Asciano, 16 km
Day 3: From Asciano to Serre di Rapolano, 14 km
Day 4: From Serre di Rapolano to Sinalunga, 20 km
Day 5: From Sinalunga to Farneta, 18 km
Day 6: Walk from Farneta to Cortona, 16 km
Day 7: Depart from Cortona!

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 Vescona to Asciano, 16 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.

Distance: 16 km

Elevation gain: +750/-900 m

Day 3:    From Asciano to Serre di Rapolano, 14 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.

Distance: 14 km

Elevation gain: +369/-275 m

Day 4:    From Serre di Rapolano to Sinalunga, 20 km

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.

Distance: 20 km

Elevation gain: +700/-700 m

Day 5:    From Sinalunga to Farneta, 18 km

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.

Distance: 18 km

Elevation gain: +240/-313 m

Day 6:    Walk from Farneta to Cortona, 16 km

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.

Distance: 16 km

Elevation gain: +360/-186 m

Day 7:    Depart from Cortona!

Last day included. Tour ends after breakfast.

Hotel Chiusarelli - Siena

Hotel Chiusarelli*** located in the historic center of Siena finds its natural setting in a neoclassical villa built around 1870. Renovated in 2013, the Hotel offers spacious and clean rooms equipped with bathroom with tub or shower, air conditioning/heating, telephone, rooms with Wi-Fi Internet and TV with Sky Vision. It does not have an elevator to reach the rooms. Quality buffet breakfast.

Hotel La Pace - Asciano

Let yourself be captivated by the atmosphere of the hotel "La Pace": a welcoming environment, which maintains the original "rustic" style, able to harmonize with the most modern comforts and with a quality of service that pays attention to the smallest details. The indoor garden and swimming pool are the perfect crowning glory for a totally relaxing vacation, able to give you a unique experience in the heart of the Crete Senesi, among art, nature and history.

Palazzo Bizzarri - Serre di Rapolano
Palazzo Bizzarri - Serre di Rapolano

This beautifully restored house,the Palazzo Bizzarri,was bougth by the proprietors, Lucia and Giuliano Civitelli, who live here with them two littles girls. The main part of the house is a 1200 tower and there is an old, romantic walled garden.When Lucia and Giuliano bought the palazzo, they also acquired all the original furniture,curtains,crockery and linen and felt it was all too perfect to change

B&B Maison Tuscany - Sinalunga
B&B Maison Tuscany - Sinalunga
Hotel Farneta - Farneta

The perfect environment for a quiet relaxation, surrounded by friendliness and cordiality: this is the atmosphere you will find at Hotel Farneta!

Hotel Farneta in Cortona Camucia is built on a hill overlooking the beautiful landscapes of the Valdichiana: surrounded by nature, it is the ideal place to spend quiet days of relaxation or a comfortable stay during conferences or business trips. It also has a large parking lot and its own park, as well as a cool porch with comfortable chairs and tables.

Hotel San Michele - Cortona
Hotel San Michele - Cortona

More than a hotel, this is a big cozy house. Located in the ancient Baldelli Palace, it has been restored with appropriate regard for the original architectural features. The specialist press and guidebooks consider this hotel a true “Concentration of Cortona’s history” and the Italian Ministry of Art listed it as a “National Monument”.

The hotel includes 40 rooms of various types. Each room is different and features ancient furniture, as well as the most modern services and comforts.

practical info

You can find more information in the "accommodation" section: we always select your accommodation for their character and comfort. You will always be booked in a private, en-suite room, with breakfast included. 

Luggage transfer (max. 20 kg)  from one hotel to the hotel is included in the price. 

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

Thanks to our special APP, you will be able to follow the track of the whole trip on your mobile phone, with no need for internet. GPS tracks are available on request.


What is included

  • 6 Nights in double room in **/*** hotels , B&B and agriturismi with breakfast
  • luggage transportation from hotel to hotel
  • maps and detailed description of the itinerary
  • Medical and luggage travel insurance
  • 24h phone assistance

What is not included 

  • Transfers to the starting location and from the arriving location of the tour
  • lunches and dinners, if not otherwise stated
  • visits and entrance fees - tips
  • personal expense
  • possible sojourn taxes
  • everything that is not mentioned in the "What is included" section.

Optional Services

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

  • Single room supplement
  • cancellation insurance
  • Transfers to reach the starting location or to leave the arriving location of the tour, which will be quoted on request.
Is this trip for me?

An enchanting trip through the most iconic landscapes Tuscany has to offer - soft hills, Reinassance city, wineries and quaint hilltop villages. We recommend this trip if you are passionate about art and culture and are well trained or have already done a walking holiday, otherwise the ups and downs and daily lenght of the walks may result a bit challenging. 

S-Cape Countryside Travels srl
Borgo Allegri 16R
50122 Firenze FI
P. IVA 05227330486

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