Once known as Porta San Michele (St. Michael Gate) or Porta Cortonese, Porta Romana (Roman Gate) constitutes one of the entrances to the town of Castiglion Fiorentino.
The original structure dates back to the 14th century, but it was almost entirely destroyed during the bombings of 1944: it was rebuilt after the war, trying to faithfully reproduce the original forms.
In contrast, the statue of St. Michael the Archangel - whose copy is currently in the niche above the pointed arch - was miraculously found intact among the rubble, a fact that for a long time the citizens of Castiglion Fiorentino considered a miracle.
The polychrome wooden original, made in the early decades of the 14th century is preserved in the Municipal Art Gallery.
In the past, four coats of arms were placed above the door, depicted in a manuscript by local historian Giuseppe Ghizzi: one represented papal rule, another represented Perugian rule, and the other two are difficult to interpret.