Itinerary
- Day 1
Terontola-Cortona to Cortona
You'll arrive at Terontola-Cortona train station at 14:00 and get a ride to a local cafe for a quick stop. From there, it's a short walk to the farmhouse where you're staying for the week. After getting settled and unpacking your things, head out to the gardens for drinks before dinner. It's a nice way to ease into the trip and meet everyone.
- Start point
- Stazione Terontola-Cortona, Località Landrucci, 124, Cortona, Arezzo 52044, Italy (Terontola Train Station, 14:00)
- Meals
- Dinner
Included Activities
- Transfer from Terontola-Cortona train station to local cafe
- Walk to farmhouse
Landmarks Terontola-Cortona Station 
- Day 2
Cortona
This morning you'll explore Cortona's ancient Etruscan burial tombs and learn about Etruscan culture from a local perspective. Then you'll hike the lower flank of Monte Egidio, walking through olive groves and oak forests with streams and old stone houses scattered along the path. After that, stop at the 12th-century Hermitage of Saint Francis to enjoy the quiet atmosphere. Later, head into Cortona town itself to walk around the streets and get a feel for the place.
- Meals
- Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner
Included Activities
- Visit Etruscan burial tombs
- Hiking trail on Monte Egidio lower southern flank
- Exploration of Hermitage of Saint Francis
- Guided tour through Cortona
Landmarks Etruscan Burial Tombs Monte Egidio Hermitage of Saint Francis Cortona - Day 3
Montepulciano
You'll walk between two medieval walled hill towns, Monticchiello and Montepulciano, connected by trails cutting through farmland. Start at Monticchiello with its famous zigzag cypress-lined road, then explore the narrow streets, fortress, ruined towers, and 13th-century gothic church. After that, continue on to Montepulciano, a busy town where the main street winds for about 1.5km up to Piazza Grande at the top. The whole route gives you a real sense of how these towns sit in the landscape.
- Meals
- Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner
Included Activities
- Walk through Monticchiello
- Exploration of Monticchiello fortress and towers
- Visit to 13th-century gothic church
- Walk to Montepulciano
- Exploration of Piazza Grande
Landmarks Monticchiello Montepulciano Piazza Grande 
- Day 4
Rapolano Terme
A local guide will take you through Siena's historic center, showing you one of the world's most beautiful cathedrals and walking the medieval streets. You'll have free time for lunch and checking out any museums that interest you. In the afternoon, transfer to Rapolano Terme to relax in the hot thermal baths and swim in the healing waters while watching the sunset over the Tuscan hills. By evening, take a stroll around town (locals call it passeggiata) and have dinner at a local restaurant.
- Meals
- Breakfast, Dinner (Dinner at a local restaurant)
Included Activities
- Historic city walking tour of Siena with local guide
- Visit to Siena Cathedral
- Thermal bath experience at Rapolano Terme
- Evening passeggiata and dinner at local restaurant
Optional Activities
- Museum visits in Siena
- Lunch in Siena
Landmarks Siena Il Campo Siena Cathedral Palazzo Pubblico Rapolano Terme 
- Day 5
Cortona
Start the day walking from the farmhouse through small hamlets and olive groves along ancient Roman basalt tracks that lead to Cortona. You'll enter the city through one of the old gates and wander the narrow streets past historic monuments. After grabbing lunch, head to the Etruscan museum with a guide who'll explain what you're looking at. The rest of the afternoon is yours to have gelato or a cappuccino at a local cafe and just sit with the atmosphere.
- Meals
- Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner
Included Activities
- Walking from farmhouse to Cortona
- Exploration of Cortona via ancient city gates
- Guided visit to Etruscan museum
Optional Activities
- Gelato or cappuccino at local cafes
Landmarks Cortona Etruscan Museum - Day 6
San Quirico d'Orcia - Bagno Vignoni
You'll head to Pienza, the Renaissance town built back in 1458 and known for its Pecorino cheese. Walk along the city walls for views over the Orcia valley, the same landscape featured in the film Gladiator. From there, walk to the medieval village of San Quirico d'Orcia, then trek the Via Francigena pilgrimage route through country lanes and woodland until you reach Bagno Vignoni. The thermal pools there have mineral-rich volcanic waters, and if you want, you can dip your feet in.
- Meals
- Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner
Included Activities
- Visit to Pienza
- Walk to San Quirico d'Orcia
- Walk along the Via Francigena
- Access to Bagno Vignoni hot pools
Optional Activities
- Dipping feet in Bagno Vignoni hot pools
Landmarks Pienza Orcia Valley San Quirico d'Orcia Bagno Vignoni Via Francigena 
- Day 7
Abbey - Buonconvento
You'll drive through the striking Crete Senesi landscape to visit an abbey with beautiful Renaissance frescoes in its cloisters, painted by Sodoma and Signorelli showing the life of Saint Benedict. After that, take a scenic walk through the desolate ochre-colored hills and make your way to Buonconvento, a walled village where you can grab gelato. It's worth pausing to think about the pilgrims who stopped in this same village centuries ago on their way to Rome along the Via Francigena.
- Meals
- Breakfast, Lunch (Gourmet picnic or packed lunch using local ingredients), Dinner
Included Activities
- Drive through Crete Senesi
- Visit to abbey with Renaissance frescoes
- Scenic walk through Crete Senesi landscape
- Visit to Buonconvento
Optional Activities
- Gelato in Buonconvento
Landmarks Crete Senesi Buonconvento 
- Day 8
Terontola-Cortona Departure
You'll get dropped off at Terontola-Cortona train station for your onward journey. Direct trains run to both Rome and Florence, each about 10 minutes away, so heading to either city is straightforward from here.
- End point
- Stazione Terontola-Cortona, Località Landrucci, 124, Cortona, Arezzo 52044, Italy (Terontola Train Station, 10:00)
- Meals
- Breakfast
Included Activities
- Transfer to Terontola-Cortona station
Landmarks Terontola-Cortona Station
