Via Lauretana Toscana,
Under the Tuscan Sun

From Siena to Cortona

91 km
7 days | 6 nights
Apr May Jun Jul Aug Sep Oct
price from
€ 858
CO2 footprint
97 Kg/person
  1. Italy
  2.  | 
  3. Self-Guided
  4.  | 
  5. Tourcode ITSW530


“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. 


  • Lose yourself in the beautiful walled villages of Cortona and Sinalunga,
  • Marvel as you walk through the Crete Senesi landscape, a real naturalal art gallery,
  • Relax bathing in the Rapolano thermal pools,
  • Celebrate the end of each walk with a glass of Brunello


Day 1

Arrive in Siena

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

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

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

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

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

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!

Depart from Cortona!

Last day included. Tour ends after breakfast.


Is this 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. 


What is included

  • 6 Nights in double room in **/*** hotels , B&B and agriturismi with breakfast
  • luggage transportation from hotel to hotel (max 1 item per person)
  • maps and detailed description of the itinerary in digital form, app
  • 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.
  • travel documentation in printed form (maps and detailed description of the itinerary), shipped to the first hotel


We work with 3* hotels, B&Bs and farmhouses that reflect our way of experiencing travel: they are comfortable and characterful structures, which we choose one by one, managed by passionate and welcoming people.

Unless otherwise specified in the travel listing, all provide private en-suite rooms with breakfast included.

Below you see some examples of the facilities used for this trip, but keep in mind that they may vary based on availability in the period. We could therefore book for you structures different from those you see listed here, but of the same category and carefully chosen according to SloWays criteria.

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.

When to travel

The  climate  in Tuscany  is  generally  very mild  with  differences  depending  on  the geography  of the  region,  from  coasts  and valleys to the continental areas.The warmest months are generally July and August,  with  temperatures  ranging  from 23°C up to 30°C; the valleys can often see higher  temperatures  and  38°C  to  40°  C  is not uncommon. While  June  and  September  offer  both  nice warm weather. Of course, there are always exceptions  or  dry  spells  that  cause  a  few days to get really hot.Spring    (April    and    May)    and    Autumn (October   and   November)   are   dry, with sunny  days  but  the  chances  of  rain  are high. The  weather  can  change  very  quickly  and you must be prepared forrain, mist, wind, fog   (and   even   hail   or   snow   at   higher elevations) –especially   in   spring and autumn. 

What to bring

Clothing and other items
You will need your regular walking/cycling gear, including some sort of reflective garment. For the evenings, smart outdoor style trousers (or shorts) are invaluable, as are quick-dry t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town.

Take as little as possible to avoid potentially lugging a heavy suitcase up three flights of stairs at the end of the day. Please be aware that laundromats (“Laverie”) are not common in rural areas, so plan to do handwashing of small items.

Lightweight walking shoes/ trainers
For wearing around towns & villages. They can also be a back-up pair.

Socks & underwear
Take only good quality socks with quick-dry and insulating qualities. Road test them before you go on the trip. Take a suitable quantity of underwear as washing facilities are limited.

Warm jacket, hat, gloves
Bring a fleece, Polartec or warm layers for the evenings especially in spring or autumn; be sure it is totally suitable for your needs.
A fleece jacket which blocks the wind (Wind-stopper) is the most preferable. In the summer months a lightweight jacket is suitable for evenings.
If you are cycling/walking in mountainous or coastal areas, even in the height of summer, the weather can change very quickly and unexpectedly and you should be prepared for fog, mist, rain, snow or hail at any time. Always take an extra layer with you, as well as a warm hat and gloves.

Waterproof jacket & trousers
If you are caught in heavy rain, with good waterproof clothing you should remain dry. Remember that most garments will lose their properties over time. Few will remain waterproof for more than five years and many deteriorate in three years or less. We recommend a rain jacket with a good hood and collar and waterproof or thermal walking/cycling trousers or tights.

Dress code
In general, you should wear suitable clothing when entering a church (in many places, it is considered unacceptable to go inside wearing shorts or a tank-top). We suggest that women carry a shawl to cover up bear shoulders or low-cut tops. It also comes in handy when your shoulders get sunburned!

It is considered inappropriate for men to go without a shirt / T-shirt (other than at the beach).

Trekking poles (adjustable)
Highly recommended. A pair works best, depending on what you are comfortable with. If you suffer from back or knee pain this should be considered essential. Remember to practise walking with your pole(s) on different types of terrain in the months preceding your trip.

Walking boots
The importance of good footwear cannot be stressed enough. Your boots should be sturdy and of good enough quality to handle all types of terrain. Lightweight boots, (cordura/leather boots) which have Gore-Tex or sympatex water-proofing are most suitable for this trip. They should provide good ankle protection and be well broken in. Waxing leather boots regularly prolongs their life.

Walking tops & trousers
We recommend walking trousers and shorts and quick-dry wicking t-shirts. These can be washed easily and will dry overnight and still look good for sightseeing or having a drink in town. Wicking T-shirts are fast drying, keep moisture away from your skin and are available at outdoor stores. You should also bring one pair of loose-fitting trousers to wear in cities and for evenings out, etc. Shorts or zip-off trousers are useful in warmer weather.

Practical info

How to arrive

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

Mobile App

Use the SloWays APP for iOS and Android smart phones in combination with the written documentation provided.

The App has the detailed tracks and maps that you can use offline and without roaming. Thanks to the phone’s internal GPS, you can check your exact position on the map, so you always know exactly where you are. It also helps you self-navigate you way while travelling. More information on how to use the App inside the roadbook documents.

The navigation features include:

  • Offline navigation. Mobile data not required after initial download
  • Accurate GPS tracks
  • Autorotation of the maps
  • Daily route summary and elevation chart
  • Panorama of the track and at street level
  • Alarm and vibration that alerts you in case you go off track.
  • Emergency SMS button with position coordinates
  • Possibility to record and take georeferenced photos of problems on route alerting fellow travelers
  • Hotel information
  • Points of interest along the way
  • Historical background

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Nominee Best Specialist Tour Operator 2023
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Borgo Allegri 16R
50122 Firenze FI
P. IVA 05227330486

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