Castello Di Montecchio Vesponi

One of the best-preserved medieval castles in Tuscany dominates the valley at the foot of Castiglion Fiorentino.

Montecchio Vesponi appears from afar as a precise image of the Middle Ages: a curtain wall, regular towers and a keep rising above the hill. Its position, along a strategic route of the Valdichiana, immediately explains the strength of the fortification.

A stronghold contested for centuries

The castle was at the center of the rivalries between Arezzo and Florence and, after the Battle of Campaldino in 1289, came under the Florentine orbit. In the 14th century it also belonged to the mercenary captain John Hawkwood, known in Italy as Giovanni Acuto. The surviving walls still make it possible to clearly read the defensive organization of the complex.

The profile that accompanies the road

As it is private property, visiting opportunities may vary, but the castle remains one of the most recognizable landmarks of the territory. It can be seen from the countryside and nearby roads, especially in the hours when the stone glows with warm light. Even from outside, Montecchio tells the story of the valley like few other places.

Local selection
Experiences in this municipality

Experiences

Experiences that include Castiglion Fiorentino among the stops included in the package.

Wine(1)
Experience01
Food & WineWellness

Wine & Spa Day

Wine & Spa Day brings together Castiglion Fiorentino and Cortona in a day dedicated to taste and well-being. The first part takes place at a historic wine…

Castiglion Fiorentino · CortonaFromCost per person starting from € 100.00
E-bike photo-12
Experience02
Slow TourismNature & Outdoor

Slow Tourism in E-Bike

Slow Tourism in E-Bike offers a guided tour around Castiglion Fiorentino, along secondary roads, paths and scenic stretches chosen to observe the territor…

Castiglion FiorentinoFromCost per person starting from € 140,00
foto varie prove-50
Experience03
Luxury & BusinessFood & Wine

Luxury Valdichiana Experience

Luxury Valdichiana Experience offers two nights between Cortona and Castiglion Fiorentino, with a selection of services designed for those who seek comfor…

2 nightsCortona · Castiglion FiorentinoFromCost per person starting from € 589.00
tartufaia-108
Experience04
Food and wineNature & Outdoor

Nature and Wine

Nature and Wine is a journey through Civitella in Val di Chiana, Castiglion Fiorentino and Cortona, built around the relationship between countryside, vit…

Civitella in Val di Chiana · Castiglion Fiorentino · CortonaFromCost per person starting from € 290.00
tartufaia-39
Experience05
Art and culture

Towers and Fortresses

Towers and Fortresses crosses six municipalities, following the architecture that for centuries controlled roads, borders and valleys. The Fortezza del Gi…

Cortona · Castiglion Fiorentino · Lucignano · Marciano della Chiana · Monte San Savino · Civitella in Val di ChianaFromCost per person from € 210.00 (minimum 5 participants)
tartufaia-41
Experience06
Art and cultureNature & Outdoor

Among Castles, Strongholds and Panoramas

Among Castles, Strongholds and Panoramas connects Castiglion Fiorentino and Civitella in Val di Chiana following fortifications, towers and ancient routes…

1 dayCastiglion Fiorentino · Civitella in Val di ChianaFromCost per person from € 125,00
foto varie prove-21
Experience07
Art and culture

Among the Etruscans and the Hills of Valdichiana

Among the Etruscans and the Hills of Valdichiana begins in Cortona, one of the most important cities for understanding Etruscan civilization. The guided t…

1 dayCortona · Castiglion FiorentinoFromCost per person starting from € 85,00
tartufaia-126
Experience08
Food & WineWellness

Between Vineyards and Wellness in the Heart of Valdichiana

Between Vineyards and Wellness in the Heart of Valdichiana begins in the countryside of Castiglion Fiorentino, among rows of vines and rural landscapes. T…

1 dayCastiglion Fiorentino · CortonaFromCost per person starting from € 150,00
tartufaia-118
Experience09
Food and Wine

Between Vineyards, Flavours and Tuscan Landscapes

Between Vineyards, Flavours and Tuscan Landscapes crosses the countryside of Castiglion Fiorentino and Monte San Savino to tell the story of the connectio…

1 dayCastiglion Fiorentino · Monte San SavinoFromCost per person starting from € 110.00
tartufaia-47
Experience10
Art and culture

Valdichiana Hidden – Journey into the Underground

Valdichiana Hidden — Journey into the Underground connects Cortona, Lucignano, Monte San Savino and Castiglion Fiorentino through places that tell the sto…

Cortona · Lucignano · Monte San Savino · Castiglion FiorentinoFromCost per person starting from € 160.00
E-bike photo-12
Experience11
Slow TourismNature & Outdoor

Valdichiana Outdoor Collection

Valdichiana Outdoor Collection offers two nights between Castiglion Fiorentino and Civitella in Val di Chiana, following trails that cross woods, olive gr…

2 nightsCastiglion Fiorentino · Civitella in Val di ChianaFromCost per person starting from € 350,00