Some Tuscan castles are famous. Others remain surprisingly overlooked. Castello di Montecchio Vesponi belongs firmly in the second category — and yet it's the one we look out at every evening from the gardens here at Casa Fiordalisi.
Rising above the Valdichiana between Castiglion Fiorentino and Cortona, its towers have dominated the surrounding countryside for nearly a thousand years. Despite its extraordinary history, relatively few visitors ever make the short journey to explore it — which is exactly what makes it worth the detour.
A Castle Above a Lake
The landscape surrounding Montecchio Vesponi looked very different to the one its builders knew. The fertile valley that stretches below the castle today was once largely underwater. Through much of the Middle Ages, the valley floor was marshland and shallow lake, and from the battlements the guards would have watched water and wetlands rather than vineyards and sunflower fields.
The position was strategically perfect: whoever controlled these heights controlled movement through one of Tuscany's most important corridors. The unusual landscape even drew the attention of Leonardo da Vinci, who studied the region and produced detailed maps of the Valdichiana as part of his investigations into water management. It was only later, beginning under the Medici, that ambitious drainage projects transformed the valley into the agricultural landscape we see today. The lake disappeared. The castle remained.
Origins in an Uncertain Age
The first fortifications here likely date from the early medieval period, when communities sought refuge on elevated ground during centuries of instability. By the 10th and 11th centuries, Montecchio Vesponi had become an important defensive stronghold in genuine border country, with power shifting constantly between local noble families, bishops, city-states and military leaders. What visitors see today wasn't built all at once — it evolved gradually as successive generations expanded and adapted the fortress to changing political realities.
This was not simply a fortified residence. It was a small village enclosed within defensive walls — families lived here, artisans worked here, livestock was sheltered here.
More Than a Castle
One of the most fascinating discoveries to emerge from recent archaeological work is the extent to which Montecchio Vesponi functioned as a complete community, with streets, workshops, domestic buildings and all the infrastructure required for daily life. Excavations undertaken in collaboration with professional archaeological teams, and supported by the current owners, continue to uncover evidence of these forgotten communities — every season reveals new details about how people lived, worked and survived within the fortress.
Wars, Mercenaries, and a Romantic Revival
Like much of Tuscany, Montecchio Vesponi spent centuries caught between rival powers, passing back and forth between the city of Arezzo and the expanding ambitions of Florence. Its walls and towers still reflect that turbulent history, strengthened by each generation in response to new threats.
One of the most intriguing chapters involves the celebrated English mercenary captain Sir John Hawkwood, known in Italy as Giovanni Acuto — one of the most famous condottieri of the 14th century, whose campaigns shaped politics across much of Italy. At one stage Montecchio Vesponi passed into his possession, a reminder that this little corner of Tuscany was never as isolated as it might appear.
As warfare evolved, the castle gradually lost its military importance and entered a long period of decline. The crenellations and battlements visible today are partly the result of 19th-century restoration, when romantic enthusiasm for the Middle Ages swept Europe and the Del Balio family — whose stewardship continues today — began the work of preservation that still continues, hand in hand with ongoing archaeological research.
Visiting the Castle
- OpeningGuided visits during selected periods, including special openings throughout June
- What's includedAccess to areas normally closed, plus insight into ongoing archaeological work
- Check aheadFollow @castellomontecchiovesponi on Instagram for current dates and tours
- From Casa FiordalisiJust a few minutes' drive — visible from our gardens
Exploring the Valdichiana
The castle sits in one of Tuscany's most underrated regions. The Valdichiana lacks the international profile of Chianti or the Val d'Orcia, but rewards visitors with equally beautiful landscapes and far fewer crowds. Nearby Castiglion Fiorentino is one of Tuscany's most attractive hill towns, with medieval streets, excellent restaurants and panoramic views across the valley. A little further on, Cortona offers Renaissance architecture, Etruscan history and some of the finest viewpoints in the region — both make wonderful additions to a day spent at the castle.
Where to Eat Nearby
- Da Muzzicone, Castiglion Fiorentino — relaxed and welcoming, especially known for its Bistecca Fiorentina. @ristorantedamuzzicone
- Osteria del Teatro, Cortona — traditional Tuscan cooking with refined presentation in one of the town's most atmospheric settings. @osteria_del_teatro_cortona
- Locanda del Molino — a leisurely lunch in a beautifully restored former olive mill in the countryside below Cortona. @locandadelmolino
Why Visit?
Many Tuscan castles are admired simply for their architecture. Montecchio Vesponi is different — its appeal lies in the layers of history that continue to emerge. A medieval fortress built above a vanished lake. A village hidden within defensive walls. A connection to Leonardo da Vinci. A chapter involving one of Europe's most famous mercenary commanders. And an archaeological story that is still unfolding.
For visitors willing to venture just a few minutes beyond Casa Fiordalisi, Castello di Montecchio Vesponi offers something increasingly rare in Tuscany: a genuine sense of discovery.
