Itinerary
- Day 1
Buonconvento
When you arrive in Buonconvento, head to your hotel and drop off your bags. If timing works out and you get there before late afternoon, take some time to walk around this medieval town with its 14th century walls still intact. The narrow streets have a lot of history packed in, and there's a museum focused on religious art if that interests you. Spend the evening getting oriented and grabbing dinner somewhere local.
Optional Activities
- Visit the Museum of Religious Art in Buonconvento
- Explore the narrow streets and medieval architecture of Buonconvento
Landmarks/POIs Buonconvento Museum of Religious Art, Buonconvento - Day 2
Asciano
Today starts your hiking through the rolling hills of Crete Senesi on dirt and gravel paths. The landscape opens up nicely as you walk, and you'll pass through Chiusure before having the option to detour to the Abbey of Monte Oliveto Maggiore if you want. By evening you'll finish in Asciano, a quieter spot where you can rest up after the day's walking.
- Meals
- Breakfast
Included Activities
- Guided hike through Crete Senesi
- Visit to Abbey of Monte Oliveto Maggiore
Landmarks/POIs Crete Senesi Chiusure Abbey of Monte Oliveto Maggiore Asciano - Day 3
Crete Senesi
Continue hiking through Crete Senesi with its distinctive rolling terrain that has an almost lunar quality to it. You're on similar dirt and gravel paths, and the views stretch across the whole area. Along the route you'll spot elegant villas and old country houses scattered throughout, which adds character to the walk.
- Meals
- Breakfast
Included Activities
- Guided hike through Crete Senesi
Landmarks/POIs Crete Senesi - Day 4
Pienza
This is one of the most well-known routes in the area, using gravel roads and dirt tracks. Make a stop at Petroio, a medieval village that sits on a hilltop in a cone shape with old houses, palaces, and churches throughout. The golden sandstone tower stands out. After that, head toward Pienza where the views over Val d'Orcia are really something to take in.
- Meals
- Breakfast
Included Activities
- Guided hike to Pienza
- Visit to medieval village of Petroio
Landmarks/POIs Petroio Pienza Val d'Orcia 
- Day 5
Montepulciano
Today's hike is a bit easier as you go from Val d'Orcia to Val di Chiana, mostly on gravel paths without major elevation gain. There's a short detour option to Monticchiello if you want. You'll end up in Montepulciano where you can unwind and try the local red wine that the town is known for. Pienza itself is a UNESCO World Heritage site with Renaissance architecture, pecorino cheese, and truffles if you haven't explored it yet.
- Meals
- Breakfast
Included Activities
- Guided hike from Val d'Orcia to Val di Chiana
Optional Activities
- Visit to hamlet of Monticchiello
- Wine tasting of Montepulciano wine
Landmarks/POIs Pienza Val d'Orcia Val di Chiana Monticchiello Montepulciano 
- Day 6
Sarteano
A short bus ride gets you to the starting point near Chianciano Terme. The hike itself is easy with very little elevation change, mostly winding through forests with some viewpoints looking out over Val d'Orcia and Val di Chiana. You finish in Sarteano, an ancient Etruscan town where you can check out the Etruscan museum if you have energy left.
- Meals
- Breakfast
Included Activities
- Bus transfer to hiking starting point
- Guided hike through forests to Sarteano
Optional Activities
- Visit to Etruscan Museum in Sarteano
Landmarks/POIs Chianciano Terme Val d'Orcia Val di Chiana Sarteano Etruscan Museum, Sarteano - Day 7
Chiusi
You're hiking across Val di Chiana today on gravel roads and dirt tracks through hills and plains. There's a detour to the Necropoli delle Pianacce if archaeology interests you, and Chiusi has an Etruscan Museum worth visiting. This town down in southern Tuscany was hugely important to the Etruscan Empire, and you can see how Etruscan, Roman, and medieval influences all exist together there.
- Meals
- Breakfast
Included Activities
- Guided hike through Val di Chiana
Optional Activities
- Visit to Necropoli delle Pianacce
- Visit to Etruscan Museum in Chiusi
Landmarks/POIs Val di Chiana Necropoli delle Pianacce Chiusi Etruscan Museum, Chiusi 
- Day 8
Departure
After breakfast on your final morning, the tour wraps up. You'll head to the airport using public transport and depart.
- Meals
- Breakfast
