8-Day Hiking Vacation in Val d’Orcia

Val d’Orcia Hiking Vacation: From Montepulciano to Siena in 8 Days

8-day hiking trip from Montepulciano to Siena

Hills covered with cypress trees, medieval towns, vineyards with Brunello grapes: welcome to the Val d’Orcia. During this 8-day self-guided hiking tour from Montepulciano to Siena, you’ll discover the most beautiful part of Tuscany, step by step.

Do it yourself or work with a local specialist

You can easily arrange this hiking trip on your own; we’ve described it below as organized by our local specialist: you’ll set your own pace, without a guide, but with peace of mind—your accommodations are arranged, your luggage will be transported, and you’ll receive clear route descriptions. Request a quote now.

Highlights of the 8-Day Hiking Vacation in Val d’Orcia

  • Medieval and Renaissance towns such as Montepulciano, Pienza, and Montalcino
  • Take a walk through the Val d’Orcia, a UNESCO World Heritage Site
  • Enjoy the peace and quiet of the countryside and the hospitality of the locals
  • Sample regional specialties such as pecorino, truffles, and the famous Brunello wine
  • Thermal baths, abbeys, and panoramic views at every stage
  • Accommodations in 3- and 4-star hotels and agriturismos
  • Easy to moderately challenging hikes (up to 5 hours per day)

Why go hiking in the Val d’Orcia?

It’s no wonder the Val d’Orcia is a UNESCO World Heritage Site. This iconic Tuscan landscape is a living postcard: rolling hills, rows of cypress trees, sun-drenched vineyards, and historic hilltop towns. Read more about the Val d’Orcia here.

On this trip, you’ll hike along quiet country roads (the famous strade bianche), through dense forests, past hot springs and abbeys. And you’ll enjoy the comfort of lovely accommodations and luggage transport.

Val d’Orcia Day-to-Day Hiking Vacation: From Montepulciano to Siena

Day 1: Arrival in Montepulciano

Your journey begins in the charming town of Montepulciano, a Renaissance town perched on a hill overlooking the surrounding vineyards. It’s easily accessible by train and bus from Rome, Florence, or Pisa. Take some time to wander through the narrow streets and savor your first glass of Vino Nobile.

You’ll be staying at the Hotel il Duomo.

Day 2: Hike from Montepulciano to Pienza

Distance: 13–15 km | Duration: approx. 4 hours
Today marks the start of your first day of hiking. You’ll leave Montepulciano via a quiet route toward the charming town of Monticchiello, where you can stop for a cappuccino or lunch. From there, you’ll continue on to Pienza, a perfect example of Renaissance urban planning.

Culinary tip: Try a piece of Pecorino di Pienza with local honey and walnuts.

Overnight stay at the Piccolo Hotel La Valle

Day 3: From Pienza to Bagno Vignoni

Distance: 12 km | Duration: approx. 4 hours
A leisurely hike through the typical Tuscan countryside, with oak forests, olive trees, and fields full of fragrant herbs. You’ll end the day in Bagno Vignoni, famous for its warm thermal baths in the middle of the village square.

Wellness Tip: Enjoy a natural spa afternoon!

Overnight stay at La Locanda del Loggiato B&B

Day 4: From Castelnuovo dell’Abate to Montalcino

Distance: 13 km | Duration: approx. 5 hours
After a short transfer, you’ll hike along scenic trails to the imposing Sant’Antimo Abbey. This is followed by a beautiful hike toward Montalcino, where you’ll be rewarded with a fine glass of Brunello.

Overnight stay at the Il Giglio Hotel

Day 5: From Montalcino to Buonconvento

Distance: 15–18 km | Duration: approx. 5 hours
Today you’ll hike through the heart of the Brunello region, past vineyards and olive groves. The route ends in the rustic town of Buonconvento or at a nearby agriturismo.

Tasting tip: Try a bruschetta made with olive oil from our own orchard.

Overnight stay at Agriturismo Pieve a Salti

Day 6: Circular hike to Monte Oliveto Maggiore

Distance: 14 km | Duration: approx. 5 hours
After a short transfer, you’ll visit the impressive Monte Oliveto Maggiore Abbey. The red-brick buildings stand out beautifully against the rugged landscape of the Crete Senesi. You’ll walk back to your lodging for a quiet afternoon.

Art tip: Check out Luca Signorelli’s frescoes in the monastery.

Overnight stay at Agriturismo Pieve a Salti

Day 7: Hike to Siena via Arbia

Distance: 10 km | Duration: approx. 4 hours
Today, your hiking adventure ends with a hike to Arbia, followed by a short train ride to Siena. The city welcomes you with its beautiful medieval center, the famous Piazza del Campo, and the magnificent Duomo.

Overnight stay at Hotel Chiusarelli

Day 8: Departure from Siena

This wonderful walking tour comes to an end after breakfast. Of course, you can extend your trip on your own, and if you have a car parked in Montepulciano, you can easily take the train back from Siena (about 2.5 hours).

Practical Information for a Hiking Vacation in Val d’Orcia

  • Price per person based on 2 people: €983 (from April 1 to October 31)
  • Price for a solo traveler: €1,610
  • Price for a triple room: €854 per person
  • Best time to visit: April through October
  • Daily departures available
  • Level: easy to moderate (daily distances of 10–18 km)
  • Luggage transport included (max. 1 piece per person; drop-off by 8:30 a.m. at the latest; delivery at the next overnight stay around 4:00 p.m.)
  • 3 transfers included (Bagno Vignoni–Castelnuovo dell’Abate, Buonconvento–Monte Oliveto Maggiore, Buonconvento–Monteroni d’Arbia)
  • Accommodations: charming 3- and 4-star hotels and agriturismos
  • Directions (digital) / app included
  • Meals: breakfast included; plenty of opportunities for local lunches and dinners
  • Trip duration: 8 days (7 nights)
  • Starting point: Montepulciano (via Chiusi)
  • Final destination: Siena
  • Additional options: transfer from Arbia to Siena, €125 per person
  • Prices are based on the accommodations listed and include breakfast, subject to availability.
  • Prices do not include the tourist tax. You pay that on-site at the hotel.

Request a quote for an 8-Day Hiking Vacation in Val d’Orcia

When you request a quote, we’ll forward it to our local partner, who will confirm the price and availability directly with you (in English). If you agree, you confirm the trip. You pay the same price as if you were booking directly. You’ll handle the rest of the booking and payment directly with the local provider (with whom we have a good working relationship and established agreements).

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Preparation & Tips

Being in good physical shape will make your trip even more enjoyable. Start hiking training a few weeks in advance, and try walking with your daypack. Check your hiking boots beforehand and break them in well. A hiking pole can come in handy on the gravel trails (strade bianche).

8-Day Hiking Vacation in Val d’Orcia on the Map

Sustainable travel in Tuscany

You’ll make your own way to Montepulciano. Hiking is one of the most sustainable ways to explore Tuscany. You can easily reach Montepulciano by public transportation and continue your journey from Siena afterward. The carbon footprint for this trip is only 95 kg per person—a fraction of that of a car vacation.

Madelon Seignette - author

About the author

Madelon Seignette

With a passion for travel and photography and over 30 years of experience in the travel industry, I love to share my special nature travel tips. Travel is wonderful and important, you meet new people and cultures and it opens your view of the world.

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