This article aims to give an overview of the Arts and Humanities Research Council funded research project, Richard Demarco’s The Italian Connection, based at Duncan of Jordanstone College of Art and Design at the University of Dundee, and to explore – albeit briefly – one of the most significant cultural relationships established by the Italo-Scottish artist, gallerist, educator, cultural entrepreneur Richard Demarco during his career – his relationship with the city of Venice. In particular, the article highlights his germinal collaboration with the historic Venetian Galleria del Cavallino, and examines using archival documents the early stage of this partnership. The most relevant events that promoted Italian contemporary visual art and theatre in Scotland through the Richard Demarco Gallery also include: Contemporary Italian Art, in 1967, in collaboration with the National Gallery of Modern and Contemporary Art in Rome; the first solo exhibition of Mario Merz in Scotland in 1988, and of Mimmo Rotella in 1990. The project started in 2018 aims to investigate and retrace Demarco’s most relevant Italian connections from a multi-disciplinary perspective to the benefit of academia and the general public.