This article focuses on the transformation of icons as means of religious expression that takes place in the Ionian Islands during the second half of the seventeenth and throughout the eighteenth century. The increasing number of ex-voto produced in that period, the emphasis on narration and pathos, the didactic character as well as the enrichment of iconography with elements deriving from the ritual practice radically alter the content of icons. The very beginning of this evolution must be sought in the immigration of artists of the Cretan School to the Ionian Islands, spanning from the years of the Cretan War to the period that followed the fall of Candia (present Herakleion). The Post-Byzantine painting of the Ionian Islands gradually departs from the morphological and ideological characteristics of the traditional icon, which thus becomes old fashioned and incompatible with the religious feelings of an evolving society. As a result the Ionian School of painting, leaving behind even the last hangover of the Byzantine tradition, adopts means and modes of painting entirely based on Western models.