The relationship between modern Italian art and the development of easel painting and sculpture in the Mediterranean Arab world have hardly been explored by art historians; little is known about how much Italian artists and institutions have contributed to the formation of style, taste, and artistic consciousness, as well as specific techniques. The present study was started in order to trace the history and evolution of these artistic relations, and to delineate and evaluate their importance and significance specifically in the Mediterranean Mashrek (Lebanon, Syria, and Egypt). It was in this area in fact, that the interest for easel painting first emerged, exercising the deepest influence on the local cultures, and Arab painters of noteworthy talent and originality emerged who in turn trained a later generation of artists. After a preliminary discussion of the relationship between Italy and the Arab-Mediterranean world which addresses the perception of Italy by Arab intellectuals and artists and the very notion of “art” prevalent in the Arab world at the dawn of the modernist era, this study goes on to discuss the case of Lebanon. The initial contacts and exchanges occurred in fact with Lebanon, where Arab painters first emerged towards the end of the 19th century. After Daud Corm, who arrived in Rome in 1871 to study with Roberto Bompiani, as many as 82 artists are listed by the Association of Lebanese graduates as having graduated or studied extensively in Italy. Egyptian and Syrian modernism are then discussed, highlighting the many major artists who studied in Italy or, in Egypt’s case, were trained by Italian artists who had emigrated to Alexandria. The study concludes with a reflection on the complexity of the present situation, characterized by an unprecedented richness and diversity of styles and a “mixed,” updated artistic culture in constant evolution and transformation.