
Gratis gids 10 verborgen natuurplekken in Europa
Gratis gids 10 verborgen natuurplekken in Europa. Meld je aan voor onze nieuwsbrief en ontvang inspirerende reistips en routes voor je volgende groene reis.
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).
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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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.
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Get inspired
Are you looking for the most beautiful hiking and biking routes? Or do you want information about traveling by train or advice for the most beautiful road trips through nature. Get inspired for your next trip in green; ideas for planning your own trip or opting for an organized trip.