Itinerary
- Day 1
Siena
You'll arrive in Siena and get settled at your hotel. If timing works out well, there's time to wander around this medieval town on your own, checking out the narrow streets, Piazza del Campo, and the Duomo cathedral.
Optional Activities
- Stroll around Siena city center
- Visit Piazza del Campo
- Visit the Duomo
Landmarks/POIs Piazza del Campo Siena Cathedral (Duomo) 
- Day 2
Crete Senesi Hike to Asciano
After a short transfer, you'll hike through the Crete Senesi landscape with its rolling hills, farmhouses, and cypress-lined roads. The route takes you through the Biancane di Leonina and Sito Transitorio areas before finishing in the village of Asciano.
- Meals
- Breakfast
Included Activities
- Guided hike through Crete Senesi area (approximately 23 km, approximately 6 hours, approximately 690m ascent and descent)
Landmarks/POIs Crete Senesi Biancane di Leonina Asciano - Day 3
Crete Senesi to Serre di Rapolano
This hike covers rolling hills in the Crete Senesi region where you'll see cypress trees and old stone houses throughout the day. At Rapolano, you'll have a chance to soak in the thermal baths, then continue hiking the final stretch to Serre di Rapolano.
- Meals
- Breakfast
Included Activities
- Guided hike through Crete Senesi (approximately 15 km, approximately 4 hours, approximately 269m ascent and approximately 161m descent)
Optional Activities
- Visit thermal baths in Rapolano
Landmarks/POIs Crete Senesi Rapolano Thermal Baths - Day 4
Serre di Rapolano to Sinalunga
You'll tackle a longer hike across different terrain including woods, vineyards, olive groves, and open fields with views of the Valdichiana valley. Along the way, you'll pass travertine quarries, walk through oak woods, go through the medieval village of Scrofiano, and arrive in Sinalunga.
- Meals
- Breakfast
Included Activities
- Guided hike through hilly terrain (approximately 20 km, approximately 7 hours, approximately 700m ascent and descent)
Landmarks/POIs Valdichiana Gimignanello Scrofiano - Day 5
Sinalunga to Farneta or Petrignano del Lago
The day involves hiking along country roads and through fields with drainage canals. There's an optional detour to the village of Bettolle halfway through. You'll finish at Farneta Abbey near your hotel, or alternatively take the train from Sinalunga to Montepulciano and hike to Petrignano del Lago instead.
- Meals
- Breakfast, Dinner
Included Activities
- Guided hike along country roads (approximately 18 km, approximately 6 hours, approximately 240m ascent and approximately 313m descent)
Optional Activities
- Detour to village of Bettolle
- Visit Farneta Abbey
- Alternative: Train from Sinalunga to Montepulciano and hike to Petrignano del Lago (11 km, 3 hours, 193m ascent, 117m descent)
Landmarks/POIs Bettolle Farneta Abbey Petrignano del Lago 
- Day 6
Farneta/Petrignano del Lago to Cortona
This longer but manageable hike crosses the plains and hills of Valdichiana following the ancient Via Romea Germanica pilgrimage route past small hamlets. You'll reach San Michele church before climbing into Cortona, or can take the train to Camucia Cortona station and bus into town as an alternative.
- Meals
- Breakfast
Included Activities
- Guided hike to Cortona (approximately 16 km, approximately 6 hours, approximately 360m ascent and approximately 186m descent)
Optional Activities
- Alternative route: Train from Camucia Cortona station and bus to Cortona (avoiding the final climb)
Landmarks/POIs Valdichiana Via Romea Germanica San Michele Church Cortona 
- Day 7
Departure from Cortona
The tour finishes after breakfast in Cortona, and you'll depart from there.
- Meals
- Breakfast
