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.
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.
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.
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.
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
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
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
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
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
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
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).
Als je een offerte aanvraagt, sturen we deze door naar de lokale partner en zij bevestigen direct aan jou de prijs en beschikbaarheid (Engelstalig). Als je akkoord gaat, bevestig je de reis. Je betaalt dezelfde prijs als wanneer je direct reserveert. Verdere afhandeling van de reservering en betaling regel je met de lokale leverancier (met wie wij goed contact en afspraken hebben).
"*" geeft vereiste velden aan
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).
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.
Met een passie voor reizen en fotografie én meer dan 30 jaar ervaring in de reisbranche, deel ik graag mijn bijzondere natuur-reistips. Reizen is heerlijk en belangrijk, je ontmoet nieuwe mensen en culturen en het opent je blik op de wereld.
Nature in Central Sweden: Waterfalls, Viewpoints, and Bears Around Ytterhogdal If you drive north on the E45, you’ll pass through Ytterhogdal. Most people just drive right through here. That’s understandable—Lapland beckons. But not far from the geographic center of...
Hiking in Arouca: The Most Spectacular Hiking Trails in Portugal's Lush North 516 meters long, 175 meters above a raging river, and no turning back halfway across. That’s the Arouca 516 suspension bridge, the icon of the Arouca UNESCO Global Geopark. This geopark is...
Laat je inspireren
Ben je op zoek naar de mooiste wandel- en fietsroutes? Of wil je informatie over reizen met de trein of advies voor de mooiste roadtrips door de natuur. Laat je inspireren voor je volgende reis in het groen; ideeën om je eigen reis te plannen of te kiezen voor een georganiseerde reis.
