Thanks to its very good maintenance conditions it is to be considered the most interesting medieval fortress in the province of Arezzo and among the most beautiful in all Tuscany. The "Vesponi" name seems to derive from a contraction of the "Guasconi" surname, an Arezzo family that owned it in the 11th century, the period of the earliest fortified construction on the site of the present castle.
Its dominant position along the road that connected, and still today connects, Arezzo with Cortona caused the small fortress to be disputed between Arezzo and Florence. In the late 14th century, it became the of the abode of the famous condottiere John Hawkwood, better known with the Italian name of Giovanni Acuto.