In ancient times the island was called ‘The Island of the Magnetes’ then Pelasgia, Dolopia and later Skyros. In 340 BC the Macedonians took over the island and dominated it until 192 BC when King Philip V of Macedon and the Roman Republican forces restored it to Athens.  In c. 475 BC, Cimon defeated the Dolopians and conquered the entire island. From that date, Athenian settlers colonized it and it became a part of the Athenian Empire. The island lay on the strategic trade route between Attica and the Black Sea (Athens depended on supplies of grain reaching it through the Hellespont).  After the Fourth Crusade of 1202–1204, the island became part of the domain of Geremia Ghisi. The Byzantines retook it in 1277. After the Fall of Constantinople, Venetians ruled again the island until 1538, when it passed to the Ottoman Empire.  It became part of the new Greek state in 1830.

In 1915, Rupert Brooke, the famous English poet, was buried on Skyros then in 1918, during the Spanish flu, approximately one-third of the island’s population died in less than 30 days.