Itinerary
- Day 1
Montepulciano
You'll arrive in Montepulciano by taking a train to Chiusi, then catching a local bus or taxi up to this Renaissance hill town. Spend the day at your own pace, wandering through the streets and getting familiar with the layout. The town sits nicely on a hilltop with great views of the surrounding countryside.
- Meals
- Breakfast
Optional Activities
- Explore Montepulciano town center
- Train from Rome, Florence or Pisa to Chiusi
- Local bus or taxi from Chiusi to Montepulciano
Landmarks/POIs Montepulciano - Day 2
Montichiello - Pienza
This is your first walking day. You'll start from San Biagio church in Montepulciano and head through quiet countryside toward Montichiello, where you can stop for lunch or a cappuccino. After your break, continue on to Pienza, a UNESCO World Heritage site with beautiful Renaissance buildings. Try some local pecorino cheese and truffles while you're there.
- Meals
- Breakfast
Included Activities
- Self-guided walk from San Biagio church to Montichiello
- Self-guided walk from Montichiello to Pienza
Optional Activities
- Local meal or cappuccino in Montichiello
- Purchase local pecorino cheese in Pienza
- Purchase truffles in Pienza
- Explore Pienza Renaissance town center
Landmarks/POIs San Biagio Church Montichiello Pienza - Day 3
Pienza to Bagno Vignoni
After breakfast, follow the self-guided hiking route through forests and rolling green hills, passing through small villages along the way. The trail takes you to Bagno Vignoni and its thermal complex, where you'll have the afternoon to relax in the spa facilities. It's a nice break after a morning of walking.
- Meals
- Breakfast
Included Activities
- Self-guided hike from Pienza to Bagno Vignoni through forests and villages
Optional Activities
- Spa treatments at Bagno Vignoni thermal complex
Landmarks/POIs Bagno Vignoni - Day 4
Sant'Antimo - Montalcino
A morning transfer brings you to the medieval village of Castelnuovo dell'Abate. Check out Sant'Antimo abbey, a former Benedictine monastery with panoramic views of the region. From there, you'll walk along a scenic trail toward Montalcino, passing through shaded woodland and getting views over the Orcia Valley. Montalcino is known for its wine production, particularly Brunello.
- Meals
- Breakfast
Included Activities
- Transfer from Bagno Vignoni to Castelnuovo dell'Abate
- Visit Sant'Antimo abbey
- Self-guided walk from Sant'Antimo to Montalcino
Optional Activities
- Wine tastings in Montalcino
Landmarks/POIs Castelnuovo dell'Abate Sant'Antimo Abbey Montalcino Orcia Valley - Day 5
Montalcino
Spend the day on independent walking through the Brunello wine region around Montalcino. You'll pass vineyards and olive groves while the Tuscan landscape unfolds around you. The Crete Sensi and Buonconvento areas offer those classic rolling hills and agricultural views that make this region so distinctive.
- Meals
- Breakfast
Included Activities
- Self-guided walk through Brunello wine region vineyards and olive groves
Optional Activities
- Wine tastings at local vineyards
- Visit wineries in the Brunello region
Landmarks/POIs Crete Sensi Buonconvento - Day 6
Buonconvento
A transfer takes you to Monte Oliveto Maggiore monastery to start your self-guided hike. Spend time exploring the impressive red brick abbey and the surrounding Tuscan landscape. Then walk back to Buonconvento through countryside that feels like something from a storybook, with its mix of hills, farms, and small settlements.
- Meals
- Breakfast
Included Activities
- Transfer from Buonconvento to Monte Oliveto Maggiore
- Visit Monte Oliveto Maggiore monastery
- Self-guided walk from Monte Oliveto Maggiore back to Buonconvento
Optional Activities
- Detailed exploration of the abbey interior
Landmarks/POIs Monte Oliveto Maggiore - Day 7
Siena
After breakfast, a short transfer takes you to Monteroni d'Arbia where your final hiking trail begins. Hike through the rolling Tuscan hills and small hamlets until Siena comes into view. Once you reach Arbia station, take the train into Siena. Spend the rest of the day exploring the city, visiting the Duomo and medieval palaces. The shell-shaped Piazza del Campo is perfect for photos and getting a feel for the city.
- Meals
- Breakfast
Included Activities
- Transfer from Buonconvento to Monteroni d'Arbia
- Self-guided walk from Monteroni d'Arbia to Arbia train station
- Train from Arbia to Siena
Optional Activities
- Visit Siena Duomo cathedral
- Explore medieval palaces in Siena
- Photographs at Piazza del Campo
- Private transfer from Arbia train station to Siena (130 Euros for group up to 4 people)
Landmarks/POIs Monteroni d'Arbia Siena Siena Duomo Piazza del Campo - Day 8
Siena
The tour ends after breakfast today. The operator suggests staying extra nights in Siena if you'd like more time there. If you're heading out, you can take a local bus to Florence.
- Meals
- Breakfast
Optional Activities
- Extended stay in Siena
- Travel to Florence by local bus
