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Highlights
Walk the Tuscan countryside following the Via Lauretana Pilgrim Trail
Visit the natural, artistic and cultural treasures of the Val d’Orcia, on the UNESCO heritage.
Observe the wonderful landscapes, wide open fields, cypress lined hills and vineyards.
Explore the incredibly well preserved medieval and renaissance villages and hilltop towns along your route.
Walk the peaceful country roads, meet friendly Tuscans and taste the delicious regional culinary specialties.
Imagine walking in the Tuscan countryside, connecting the iconic towns of Siena and Cortona. Days filled with walking through Tuscany, evenings in towns and villages, enjoying world class food, wonderful wine, and incredible history. This Siena to Cortona walking tour is the trip for you.
This linear route through the Tuscan landscape of the Crete Senesi, Val d’Orcia and Val di Chiana loosely follows the Via Lauretana pilgrim trail that after Cortona continues on to Loreto in the region of Abruzzo. Passing through the most classic and photogenic of landscapes you cross a land of serene natural beauty through open farmland, deep valleys, dense forests and ancient villages.
Walk by picturesque farmhouses nestled amidst olive groves, vineyards and fruit trees on your way to the hot spring hamlet of Rapolano where you can swim in the hot thermal pools, overnight in hilltop towns and visit the heavenly medieval and Renaissance cities of Siena and city of Cortona. And don’t forget to try the divine local red Brunello and Rosso di Montepulciano.
Imagine walking in the Tuscan countryside, connecting the iconic towns of Siena and Cortona. Days filled with walking through Tuscany, evenings in towns and villages, enjoying world class food, wonderful wine, and incredible history. This Siena to Cortona walking tour is the trip for you.
This linear route through the Tuscan landscape of the Crete Senesi, Val d’Orcia and Val di Chiana loosely follows the Via Lauretana pilgrim trail that after Cortona continues on to Loreto in the region of Abruzzo. Passing through the most classic and photogenic of landscapes you cross a land of serene natural beauty through open farmland, deep valleys, dense forests and ancient villages.
Walk by picturesque farmhouses nestled amidst olive groves, vineyards and fruit trees on your way to the hot spring hamlet of Rapolano where you can swim in the hot thermal pools, overnight in hilltop towns and visit the heavenly medieval and Renaissance cities of Siena and city of Cortona. And don’t forget to try the divine local red Brunello and Rosso di Montepulciano.
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From Siena to Cortona Walking Tour Itinerary
Day 1 Arrival 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.
Overnight Location: Hotel in Siena
Distance: None
Meals: None
Day 2 Transfer to Biancane di Leonina or Vescona and walk to Asciano
After a short ride you start a long walk through the heart of the Crete Senesi area enjoying great views of the iconic rolling hills dotted with ancient farmhouses and cypress lined country lanes. You pass through the famous “Biancane di Leonina” the “Sito Transitorio”. The route to Vescona winds through gullies and ochre-coloured clay farmland; vast gently undulating wheat fields that change colour according to the season, always a spectacle to the eye. The walk ends in the village of Asciano.
Overnight Location: Hotel in Asciano
Distance: 4-6 hours, 15.5-23km, 340-690m of ascent, 310-690m of descent
Meals: Breakfast
Day 3 Walk Asciano to Serre di Rapolano optional via Rapolano Terme spa
It’s an easy walk along the heart of Crete Senesi. You can enjoy great views 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 destination of today, Serre di Rapolano.
Overnight Location: B&B in Serre di Rapolano
Distance: 4 hours, 7-15km, 269m of ascent, 161m of descent
Meals: Breakfast
Day 4 Walk Serre di Rapolano to Sinalunga
This longer walk through is on hilly terrain, with a landscape composed by woods, vineyards, olive groves and fields. Along the trail you enjoy astonishing views of Valdichiana (the valley of Chiana River). Leaving Serre di Rapolano, you 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.
Overnight Location: B&B in Sinalunga
Distance: 7 hours, 20km, 700m of ascent, 700m of descent
Meals: Breakfast
Day 5 Walk from Sinalunga to Farneta
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. Midway you may wish to make a short detour to visit the village of Bettolle. At the end of the walk don’t miss out on a visit to the Abbey of Farneta located in front of the hotel.
Overnight Location: Hotel in Farneta
Distance: 6 hours, 17km, 240m of ascent, 313m of descent
Meals: Breakfast
Day 6 Walk from Farneta to Cortona
It’s a long but gentle walk through the planes and hills of Valdichiana. From here on, the path coincides with the another ancient pilgrim route: 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.
Overnight Location: Hotel in Cortona
Distance: 6 hours, 16km, 360m of ascent, 186m of descent
Meals: Breakfast
Day 7 Departure from Cortona
Last day included. Tour ends after breakfast.
Overnight Location: None
Distance: None
Meals: Breakfast
2026 Pricing for From Siena to Cortona Walking Tour
The departures are available from April 1 to October 31, 2026.
Accommodation on From Siena to Cortona Walking Tour
Enjoy your stay in selected 3* and 4* hotels and agriturismo. Some of the accommodations chosen have a swimming pool and internal restaurant. All rooms in the accommodations have en-suite facilities. Throughout the trip, there are plenty of opportunities to taste both the great local food and a wide array of prestigious wines of the region.
Single Rooms and Solo Travelers
Rooms are double occupancy. You can pay a supplement to have a private room where possible. Solo travellers may be required to pay a supplement.
Night 3
B&B Palazzo Bizzarri in Serre di Rapolano
B&B Palazzo Bizzarri in Serre di Rapolano: an elegant retreat steeped in history, offering a blend of Tuscan charm, modern comfort, and a serene atmosphere for guests exploring the enchanting surroundings and rejuvenating in the nearby thermal springs.
What’s Included in the From Siena to Cortona Walking Tour?
Meals
6 breakfasts and 1 dinner are included.
Accommodations
Accommodations for 6 nights are included.
Transportation during the Tour
Luggage transfers are included. This tour also includes one personal transfer on day 2 (Siena to Biancane di Leonina). Any other transfers are not included.
Also included
- Digital information package
- Emergency phone support
Not included
- Getting to and from the trailhead
- Travel insurance
- Flights
- Guide services
- Meals, drinks, or snacks not previously mentioned
- Visas if required
- Tourist taxes
Optional Extras
- Printed travel documents
- Optional extra nights
- Single room upgrades
- How hard is the From Siena to Cortona Walking Tour?
- Do I need a visa to travel to Italy?
- Are meals included on the From Siena to Cortona Walking Tour?
- Do I need insurance?
- How do I get to Siena to start this tour?
- Is the From Siena to Cortona Walking Tour in English?
- Where does the From Siena to Cortona Walking Tour end?
- Do I need special vaccines to travel to Italy?
- Are there any travel restrictions for Italy?
We rate the difficulty of this tour as a 3 / 5. The route is quite easy, with ups and downs typical of the Tuscany’s rolling hills. The whole itinerary is mostly on paths and gravel roads (strade bianche), even if you will find some sections on asphalted road. Some may find the distances challenging (up to 23km daily), but some walks can be shortened if requested in advance.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
6 breakfasts and 1 dinner are included.
Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover hiking. Get your travel insurance.
The closest International Airports to get to Siena are: Florence “A. Vespucci” Airports and Rome Fiumicino. From the airports you can take a train and then busses to reach Siena.
This tour is not guided; however, the digital information package will be in English.
The tour ends in Cortona.
Check with your family doctor.
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
Customer Ratings
S-Cape Travel is a boutique tour operator focused on sharing the best walking, cycling, cultural and food & wine tours in Europe. Book one of their self-guided tours to live La Dolce Vita for a week or two, as you walk or cycle around Europe, enjoying incredible views and amazing food and wine.
