His first contact with the arts came in the form of religious icons in the archbishopric in Nicosia, where he trained as an artist.

He left Italy in 1877 and went to Greece, where he enlisted as a volunteer in the Greek Army and fought for the liberation of Thessaly during the Greco-Turkish War of 1897.

With the end of Ottoman rule of Cyprus in 1878, he returned to the island and settled in Limassol, staying at the local premises of the Diocese of Larnaca.

His first poetry collection, The Weak Lyre (Greek: Η Ασθενής Λύρα), was published in 1882.

In 1883, Michaelides wrote The Fairy (Greek: Η Ανεράδα), followed by his most famous work The 9th of July 1821 (Greek: Η 9η Ιουλίου 1821),[1] a poem in the Cypriot dialect detailing the events leading to the execution of the Greek Cypriot leadership, including Archbishop Kyprianos, by the Ottoman rulers of the time: Michaelides' poetry helped establish the Cypriot dialect as a linguistic medium for written poetry.