The aim of this article is to investigate the history of visual communication and graphic materials linked to pleasure boats, from the first steps that advertising took in this sector, from the first posters, to magazines, up to how today’s social media tell about these extraordinary boats and the shipyards that produce them. During this analysis it will also be essential to talk about the main trade fair events that, around the world, allow us to admire these products and some of the most interesting installations created for some events. Many examples will be shown here in which multiple disciplines come together to tell us about these boats, therefore through an interdisciplinary approach that makes this product art, entertainment and so we become spectators. One of the objective of this research is therefore to understand what the historical evolution of the representation of these means has been, what has already been said and what the unmet needs are to lead us to new scenarios and, thus, in the direction of increasingly rich and intersectional visual communication. An experimental phase will be added as the purpose of the above: the design of a survey to be filled in to those attending a boat show, to question visitors about the visual communication related to the boating world; it will be a qualitative research that could investigate what are the opinions of those who experience this world as observers and what could be improved in its representation.