From Siena to Cortona Walking Tour

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