The best way to get an idea of the town and its history is to follow the sinuous cobbled lanes past the mansions of the Old Town to the Kastro, the highest point, and the 10th-century fortified Monastery of St. George, which stands on the site of the ancient acropolis and Bronze Age settlement. Little remains of the legendary fortress of King Lykomedes, portrayed in Skyros's two most colorful myths, though lower down on the north and southwest face of the rock are the so-called Pelasgian bastions of immense rectangular fitted blocks, dated to the classical period or later. A white marble lion, which may be left over from the Venetian occupation, is in the wall above the entrance to the monastery. This classical symbol is a reminder of when Skyros was under Athenian dominion and heavily populated with Athenian settlers to keep it that way. This part of the castle was built on ancient foundations (look right) during the early Byzantine era and reinforced in the 14th century by the Venetians.
monastery itself was founded in 962 and radically rebuilt in 1600. Today it is inhabited by a sole monk. Unfortunately, the once splendid frescoes of the Monastery of St. George are now mostly covered by layers of whitewash, but look for the charming St. George and startled dragon outside to the left of the church door. Within, the ornate iconostasis is considered a masterpiece. The icon of St. George on the right is said to have been brought by settlers from Constantinople, who came in waves during the iconoclast controversy of the 9th century. The icon has a black face and is familiarly known as Ayios Georgis o Arapis ("the Negro"); the Skyrians view him as the patron saint not only of their island but of lovers as well.