Via Lauretana Easy Under the tuscan sun asciano crete
Via Lauretana Easy Under the tuscan sun asciano crete

Under the Tuscan Sun: from Siena to Cortona, Via Lauretana easy version

7 days | 6 nights
Apr May Jun Jul Aug Sep Oct
price from
€ 896
  1. Italy
  2.  | 
  3. Hiking Tours
  4.  | 
  5. Tourcode ITSW530E

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".

If you are fascinated by these atmospheres, this journey will transform your dreams into reality. You'll encounter fig trees, cypresses, gently undulating hills, and picturesque hamlets that have always filled your imagination, and even more. Starting from Siena, renowned for its "Contrade" and the distinctive shell-shaped square, the trail leads you through the thermal baths of Rapolano, prestigious wineries offering the exquisite local "Brunello" red, the otherworldly, iridescent scenery of the "Crete Senesi," dense oak forests, and pastures adorned with cypresses and traditional farmhouses.

And not to be overlooked is Cortona, the setting of "Under the Tuscan Sun". Nestled atop a hill, this charming town has been a residence for artists and saints, Romans and Etruscans alike. It serves as the perfect conclusion to your quintessential Tuscan adventure.


  • Lose yourself in the enchanting walled villages of Cortona and Sinalunga,
  • Be amazed as you wander through the artistic tapestry of the Crete Senesi landscape,
  • Relax in the Rapolano thermal pools,
  • Toast to the conclusion of each walk with a delightful glass of Brunello.


Day 1

Arrive in Siena

Arrive in Siena

Arrive in Siena and check-in at your hotel. If you havetime, take the opportunity to explore the city renowned for its biannual “Palio” horse race, hosted in the magnificent shell-shaped Piazza del Campo—considered the most beautiful square in Europe. Visit the Duomo, an architectural gem, along with the numerous imposing medieval palaces. The narrow streets of this impeccably preserved Italian gem bring history to life as you wander through them.

Day 2

Transfer to Torre a Castello and walk to Asciano, 12 km

Transfer to Torre a Castello and walk to Asciano, 12 km

Following a short transfer, you walk through the heart of Crete Senesi. Revel in breathtaking views of the iconic Tuscan rolling hills, adorned with ancient stone houses and bordered by majestic cypress trees. Traverse the lunar landscape of "Biancane di Leonina" and the "Sito Transitorio." The path leading to Vescona winds through ravines and cultivated fields, where shade is scarce, and the predominantly clayey soil characterizes the terrain. Finally, you reach the charming village of Macigliani, perched on a spectacular balcony overlooking Siena.

Distance: 12 km

Elevation gain: +250/-360 m

Day 3

From Asciano to Rapolano Terme, 10 km

From Asciano to Rapolano Terme, 10 km

You continue your journey through Crete Senesi, where you'll delight in magnificent views of the iconic Tuscan rolling hills adorned with ancient stone houses and bordered by picturesque cypress trees. Be mindful that, in the event of rain, certain sections may become muddy and slippery due to the clay soil.

Cap off the afternoon at the thermal baths complex in Rapolano, an ideal spot to bask in the warmth of Tuscany. 

Distance: 10 km

Elevation gain: +230/-100 m

Day 4

From Rapolano Terme to Serre di Rapolano, 10 km

From Rapolano Terme to Serre di Rapolano, 10 km

Today you reach Serre di Rapolano through a quintessential tuscan landscape. Serre di Rapolano is an ancient village of byzantine and etruscan origin: visit the local grancia (an ancient fortified farmhouse).

Distance: 10 km

Elevation gain: +125/-90 m

Day 5

Transfer from Serre di Rapolano to Bettolle and walk to Farneta, 10 km

Transfer from Serre di Rapolano to Bettolle and walk to Farneta, 10 km

Today you walk along rural roads, traversing fields and the historic canals' banks, which were once dug to drain the valley for land reclamation.  At the end of the walk, it is highly recommended to visit the Abbazia di Farneta, conveniently located just across from the hotel.

Distance: 10 km

Elevation gain: +110/-110 m

Day 6

From Farneta to Camucia and bus to Cortona, 13 km

From Farneta to Camucia and bus to Cortona, 13 km

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

Distance: 13 km

Elevation gain: +90/-130 m

Day 7

Arrivederci Cortona!

Arrivederci 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. Some sections of this trip are shortened by public transport or taxi transfers, making this walk more suitable to beginners.


What is included:

  • 6 Nights in double rooms in 3/4* hotels and agritourismi with breakfast
  • luggage transportation from hotel to hotel (max 1 item per person)
  • Transfer Siena-Torre a Castello
  • Transfer Serre di Rapolano-Bettolle
  • Maps and detailed description of the itinerary in digital form, app
  • 24h phone assistance
  • Medical-luggage insurance

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
  • 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.


Hotel Chiusarelli - Siena
Hotel La Pace - Asciano
Palazzo Bizzarri - Serre di Rapolano
B&B Maison Tuscany - Sinalunga
Hotel Farneta - Farneta
Hotel San Michele - Cortona

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, et

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.

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

Wanderlust Nominee Best Specialist Tour Operator 2023
Nominee Best Specialist Tour Operator 2023
Change currency:

We accept:


We accept:

FTO ATTA member
100% Green Travelife
FTO ATTA member 100% Green Travelife

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

© 2024 SloWays. All rights reserved.
Touroperating S-Cape Countryside Travels srl Borgo Allegri 16R 50122 Firenze FI, Italy
VAT Nr 05227330486

We and selected third parties use cookies or similar technologies for technical purposes and, with your consent, for functionality and marketing (personalised ads) as specified in the cookie policy. Denying consent may make related features unavailable.