Explore the magnificent natural beauty of the Val d'Orcia region in Tuscany, walking through cypress-lined hills and vineyards, with time for tasting the wine, cheese, honey, and other culinary delights that the area is known for. Your adventure will take you through the wine-growing town of Montepulciano, then to Pienza where you can taste its distinctive Pecorino cheese, and finally to the medieval Tuscan powerhouse of Siena.


  • See Tuscan views and sip on wine in Montepulciano
  • Taste Pecorino cheese and pungent truffles in Pienza
  • Take a dip in the thermal baths of Bagno Vignoni
  • Hike to the picturesque abbey of Sant’Antimo
  • Marvel at medieval architectural masterpieces in Siena

Brief Itinerary

Day Highlights Overnight
Day 1 Montepulciano Montepulciano
Day 2 Montepulciano to Pienza Pienza
Day 3 Pienza to Bagno Vignoni Bagno Vignoni
Day 4 Bagno Vignoni to Sant’Antimo to Montalcino Montalcino
Day 5 Montalcino to Buonconvento Buonconvento
Day 6 The Abbey of Monte Oliveto Maggiore Buonconvento
Day 7 Monteroni d’Arbia to Siena Siena
Day 8 Siena  

Detailed Itinerary

Day 1: Montepulciano

Montepulciano, Italy
Montepulciano, Italy

Your walking tour will begin in a typical Tuscan hill town — Montepulciano. The town is easily accessible from Rome or Florence by catching a train to Chiusi and then transferring to a local bus or taxi to Montepulciano 13 miles (21 km) away. You'll have the night free in Montepulciano to admire the impressive Tuscan views and landscape that you'll be exploring over the next week, and try authentic Tuscan cuisine.

Day 2: Montepulciano to Pienza

Pienza, Italy
Pienza, Italy

It's time to put your hiking or walking shoes on, as you head off for day one of your tour. You'll start early from San Biagio church, following a quiet track to the peaceful village of Montichiello, where you can pause for a relaxed lunch on your way to Pienza, nine miles (15 km) away. Once you arrive in Pienza — a UNESCO World Heritage Site — you'll have time to explore the town's Renaissance architecture, sample its famous Pecorino cheese and truffles, and settle into your hotel for the night.

Day 3: Pienza to Bagno Vignoni

Bagno Vignoni, Italy
Bagno Vignoni, Italy

You'll have another full day of walking ahead of you as you wander through rolling hills, oak woods, groves of cypress trees, and pretty villages during your nine-mile (15 km) adventure from Pienza to the thermal baths of Bagno Vignoni. The natural hot springs here have been visited for centuries, and you can take a dip in the Parco dei Mulini, for the perfect dose of relaxation after a long day on the trail.

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Day 4: Bagno Vignoni to Sant’Antimo to Montalcino

Sant’Antimo, Italy
Sant’Antimo, Italy

Your next destination will be 8 miles (13 km) away, at the abbey of Sant’Antimo — a former Benedictine monastery on the Via Francigena pilgrimage route to Rome. The hike there from Bagno Vignoni will take you through riverbeds, and may prove more challenging than other parts of your walk so far, as you head into a more isolated and pastoral landscape. After more time to explore the abbey and learn more about its history, you'll transfer by car to Montalcino 6 miles (10 km) away.

Day 5: Montalcino to Buonconvento

After a hearty breakfast, you'll set off for a long day heading toward the Brunello wine-growing region and Buonconvento, 8 miles (13 km) away. Your trail will take you through vineyards, olive groves, and more Tuscan in the Crete Senesi —  a range of hills, woods, and villages south of Siena. In the late afternoon or early evening, you'll arrive in Buonconvento, a village of about 3,000 people, which is still fortified by its Renaissance-era walls.

Day 6: The Abbey of Monte Oliveto Maggior

Abbey of Monte Oliveto Maggiore

Explore the impressive abbey of Monte Oliveto Maggiore — a large Benedictine monastery — which was founded on a hilltop in 1313. You'll stroll through the rugged Tuscan landscape and explore its porticos and grounds, and after your visit, you'll make the about 6-mile (9.5 km) walk back to Buonconvento, which will take about 2 hours. 

Day 7: Monteroni d’Arbia to Siena

Siena, Italy
Siena, Italy

After a transfer to Monteroni d’Arbia you'll start your 6-mile (10 km) walk toward Arbia, where you will catch a train to Siena. Your hike will take you through a landscape of rolling hills and small hamlets, and as you get closer, you'll see the skyline of the significant medieval city, Siena, in the distance.  From Arbia, it'll be a quick 10-minute train ride to Siena, which is known for its Piazza del Campo, where the famous Palio di Siena horse race is held each year in July and August. You can people watch in the square, tour Siena's medieval duomo, and eat an authentic Tuscan meal.

Day 8: Siena

Siena, Italy
Siena, Italy

Spend your last hours soaking up the Tuscan countryside with a final early-morning walk before your tour ends after breakfast.


Map of Hiking the Hill Towns of Tuscany in Val d'Orcia: Montepulciano, Pienza, and Siena - 8 Days
Map of Hiking the Hill Towns of Tuscany in Val d'Orcia: Montepulciano, Pienza, and Siena - 8 Days