Top 9 Castles around Castiglion Fiorentino

Montecchio Vesponi Castle dominates the Val di Chio from a hill over 360 meters above sea level. With its crenellated walls, towers, and an imposing 30-meter-high square tower, it is one of the best-preserved medieval castles in Tuscany and can be recognized from afar throughout the valley. Contested for centuries by Arezzo and Florence for its strategic position on the road to Cortona, it became a Florentine stronghold after the Battle of Campaldino in 1289. In the 14th century, it was also home to the famous mercenary captain John Hawkwood. Today, the castle comes back to life with guided tours, events, and reenactments that evoke the atmosphere of the Middle Ages.

check hours as they are open only certain days

we go up towards the hill

The Girifalco Fortress is an imposing defensive structure that dominates the city of Cortona from above. Built in the 16th century to protect Cortona from external attacks, it today offers a breathtaking view of the Valdichiana. It's a perfect place for a scenic walk, take incredible photos and immerse yourself in history. The fortress also hosts exhibitions and cultural events, making it a lively and interesting place to visit.

In 963 AD, the Holy Roman Emperor Otto the Great granted the castle and its court to the Canonina Aretino. In 1040, the Castle of Policiano was chosen as a wedding gift by Pietro Eriberto, heir of the historic Ghibelline family of Azzi, to future wife Gualdrada. Only 4 years later, the castle became the property of Uguccione of the Marquises de Bourbon of Monte Santa Maria, one of the most important feudal families of the Middle Ages in Tuscany who were then appointed imperial vicars by Emperor Charlemagne. During the 15th century, the castle became the property of the Capponi family of Florence whose 16th century coat of arms can still be admired today on the ancient walls Leonardo da Vinci depicts the Policiano Castle in the “Codex Atlanticus” on the Map of the Val di Chiana. The Renaissance genius visited the castle during his trip in 1503 to discover the Arezzo area. In 1848, the castle was purchased by the Chigi Saracini, a noble banking family of Sienese origin. In 1910 all the buildings owned by Chigi Saracini were taken over by Sidney Mary Hertz of Barbolani di Montauto who transformed the Castle into a farmhouse, renovating it with architectural style of that period, which is reflected in the front facade. In the 13th century, the castle became a stopover for many travelers heading to Rome via the Via Francigena. It is thought that St. Francis of Assisi often resided in the castle during his travels from Assisi to the Franciscan sanctuary of La Verna. In 1265, Guglielmo degli Ubertini, who went down in history as "the warrior bishop", took possession of the castle and obtained the oath of obedience and loyalty from 54 men. It was the warrior bishop who led the Ghibelline army against the Guelphs in the famous battle of Campaldino in which he perished.

On the southern borders of the municipal territory of Arezzo, in a splendid panoramic position on a spur overlooking the Val di Chiana, the Vitiano Castle, better known as La Torre, still exudes great charm. Built between the end of the 10th century and the 11th century and mentioned for the first time in 1098 as part of a will, the castle was part of the vast possessions of the Marchiones held through their vassals, who here took the name Da Vitiano and they subsequently became the actual owners. In June 1153 the Arezzo militias besieged the manor, forcing the owners to sign the transfer of ownership to the Municipality and the Parish Church of Arezzo. The deed was signed on June 28 of that year. In exchange for the transfer, the ancient owners regained the fortress and its court as a fief, but they had to respect the pacts of submission and loyalty. Subsequently, the Da Vitianos moved or were forced to move to the city, to the Porta Sant'Andrea neighborhood. From some branches of the family the Perini, the Marcelli and the Dragomanni were born. The Perini also gave their name to one of the most characteristic "canti" of Arezzo, the one near Giorgio Vasari's birthplace in today's via Mazzini. According to Ubaldo Pasqui the "Annales Arretinorum Maiores" - fundamental sources for reconstructing the history of Arezzo – were written by Ser Francesco, son of Ser Astoldo di Baldinuccio Da Vitiano, one of the most famous Arezzo notaries of the early fourteenth century.

Beautiful medieval castle with lots of cycling and hiking routes connecting.

Given that the whole city of Cortona is wonderful, I highly recommend visiting this place for the architecture of the buildings and the magic of the atmosphere that the view of the Val di Chiana conveys.