Ionians were settled in Sikinos, as testified by the inscriptions found, while the various archaeological findings certify continuous human settlement from the Mycenaean period up to the present day. Sikinos was a member of the Delian League and the tax it paid did not exceed one thousand attic drachmas. It was an organized state and Solon often mentioned it as an example to the Athenians. On the island Pythian Apollo, Hermes Agoraios and Dionysus Savazios were worshiped.
During the time of the Roman conquest it hosted exiles. It was conquered by the Franks (1207-1262) and was part of the Duchy of Naxos. The Byzantines recaptured the island in 1262 and in1307 and until 1464 it was under the dominion of the Spanish house of Dacoronia. During the Rule of Franks it was also called Sikandros, a word which is probably a corrupted type of the word Sikinos.
Like the neighbouring islands, it was captured in 1537 by the famous Hayreddin Barbarossa and became an island which had to pay attribute to the Sultan. At that time it came under the control of the house Gozzadini that stayed on the island until 1617. The Ottoman conquest of Sikinos was interrupted during the Orlov period, when it was conquered by the Russian fleet (1770-1774). From 1700 until the time of the Revolution of 1821, on the island there was a French Consulate.
During the Second World War, from 1941 until 1943 the Italian administration settled in Sikino. After the capitulation of Italy it was the Germans’ turn to leave the island with the liberation in 1944.