> Trek from Pienza to Montalcino in just 3 days
> Sleep in Bagno Vignoni and Castelnuovo dell’Abate
> We arrange your accommodation before, during and after the hike
The early morning sun rises over the cypress-lined hills of Tuscany as you lace up your boots in the Renaissance gem of Pienza. Three days of winding trails, thermal springs, medieval hamlets, and world-class wine await. This is the Val d’Orcia stripped down to its essence. No fluff. Just Tuscany at its finest.
This Intense Val d’Orcia Trek is a long-weekend special. It’s the same beautiful route as the Val d’Orcia Experience but with longer stages, making it ideal for those with limited time and unlimited energy. Start with a relaxing night in Pienza, then walk through golden hills to Bagno Vignoni, dip into the magic of Castelnuovo dell’Abate, and end in Montalcino, home of the Brunello. Your bags get transferred. Your accommodations are sorted. All you need to do is show up, walk, and soak it all in. La dolce vita, with hiking boots on.
Today’s walk is full of highlights. From Pienza, you’ll descend through olive groves and cypress-lined paths to the iconic Cappella della Madonna di Vitaleta, then continue past a Gladiator filming location before reaching San Quirico d'Orcia — a great spot for coffee or lunch. After a final climb with stunning views back over the town, you’ll pass through the tiny hamlet of Vignoni Alto before descending to Bagno Vignoni, famous for its ancient thermal pool and peaceful atmosphere.
From the thermal charm of Bagno Vignoni, you head back into the heart of the Tuscan countryside. The trail leads you gently uphill toward Castiglione d’Orcia, a striking village perched high above the valley. The climb is steady and rewarding, with views that get better with every step. At the top, the ancient fortress offers a perfect spot to soak in the timeless energy of the Val d’Orcia.
Leaving Castiglione behind, the trail becomes quieter. You follow country lanes flanked by olive groves and vineyards, descending gradually to a riverbed. There’s no bridge here — you’ll need to wade across. In summer the water is usually low, but after rain, the current can pick up. Locals can advise, and if in doubt, a short taxi transfer will get you safely to the other side.
From the river, it’s a final push uphill to Castelnuovo dell’Abate. The village rises in the distance, with its abbey tower hinting at the peaceful rest that awaits.
Your final hiking day begins with a peaceful stretch past the beautiful Sant’Antimo Abbey, a timeless Romanesque church nestled in the valley. From there, you continue through gentle countryside until you reach the medieval chapel of Villa a Tolli, a quiet spot that feels frozen in time.
The path winds past vineyards and begins to climb toward Passo del Lume Spento. As you gain elevation, the views open up once more over the surrounding hills. From the pass, you enter a mix of forest and vineyard trails that lead you all the way to Montalcino, a hilltop town known for its world-famous Brunello wine and sweeping panoramas. A fitting finish to your Tuscan trek.
