The contribution of Italian art, especially Venetian, was decisive to the secularisation of art in the Ionian Islands and the shaping of the so-called Ionian School, in the context of a broader Western influence affecting all aspects of life and culture, especially on the islands of Zakynthos and Corfu. Italian influences, mainly of Renaissance, Mannerism and Baroque art, can be identified both on the iconographic and the stylistic level of artworks, with theoretical support. This article explores facets of the dialogue of secular painting in the Ionian with Italian art in the eighteenth and nineteenth centuries, focussing on works and artists that highlight significant aspects of this multilayered phenomenon and also through secondary channels that expand the horizon of analysis. Procession paintings, with their various connotations, and portraiture, which flourished in secular Ionian art, offer the most interesting material as regards the selection, reception and management of Italian models and points of reference.