Ghino di Tacco Trail: history, legend and Tuscan landscapes

Distance: ~20 km – Duration: 4.5-6 hours

The path starts from Torrita di Siena, the village where Ghino was born. Here, between the medieval walls and towers that still stand in the main square, young Ghino grew up among noble Ghibelline families, learning the arts of chivalry and military strategy. According to legend, as a teenager, Ghino secretly observed the movements of the Guelph militias to study defence tactics and ambushes.

The route crosses rolling hills, cultivated fields and olive groves, along dirt roads and mule tracks that, in the Middle Ages, allowed rapid travel between Torrita and the nearby villages. When you reach Monticchiello, a hilltop village with medieval walls, you can still sense the atmosphere of times gone by: According to local tales, Ghino found refuge from the Guelph militias here and slept in the homes of trusted friends. The central square and narrow cobbled streets were the perfect setting for his escape plans and his fame as a “gentleman thief”.

Interesting historical fact: Besides being a place of refuge, Monticchiello was also a strategic observation point: from here, Ghino could monitor the roads of the Valdichiana without being seen.

Distance: ~23.7 km – Duration: 5-7 hours

After leaving Monticchiello, the trail enters the Val d’Orcia with its woods, ravines and rolling hills. Here, Ghino di Tacco consolidated his reputation as a gentleman brigand: according to stories, he did not rob the poor and often distributed part of the loot among the communities that protected him. Some chronicles speak of daring ambushes on the convoys of Guelph nobles, always conducted shrewdly and without unnecessary violence.

After several hours of walking, you come to Contignano, a medieval village located along the Via Francigena. Here, Ghino is said to have formed alliances with the local communities, who offered him refuge and information on enemy movements. His presence helped maintain a balance between the Guelphs and Ghibellines and the inhabitants saw him as a protector, rather than a bandit.

Local legend: It is said that, in order to save a convoy of peasants from Guelph raids, Ghino once dropped a huge tree trunk onto a side path, blocking the enemy soldiers and allowing the poor to escape.

Distance: ~16.7 km – Duration: 3.5-5 hours

The last leg leads to Radicofani, the stronghold symbolising the legend of Ghino di Tacco. The final climb to the Radicofani Fortress, standing impressively on the hilltop, retraces the brigand’s historic rise to power. Here, Ghino controlled the main roads of the Val d’Orcia and defended the fortress from enemy attacks.

According to tradition, Ghino devised a system of visual signals between the fortress and the nearby villages, to warn of the approach of enemies or convoys to pillage. Today, the fortress still retains the atmosphere of the brigand’s endeavours, with towers and walkways offering views of the entire valley.

Interesting fact

According to some chronicles, Ghino was never captured in Radicofani and after his death the people continued to pass down stories of how he protected the poor and punished the rich without scruples.

Practical advice

Climb slowly to the fortress and visit it carefully; the panoramic views are a reward for your efforts and help you imagine Ghino’s tactics.

Walking along the Ghino di Tacco Trail means walking through history and legend, with breathtaking views, following in the footsteps of a man who challenged the powerful and protected the weak. Each village tells an anecdote and each hill an adventure, transforming the hike into a true journey through medieval Tuscany, where nature, culture and legend blend together in a single, unforgettable experience.