The huge transformation fostered by the current industrial revolution is changing each side of our society. In the design field, the use of digital and connected technologies improves not only the representation but also the formal references and the creative process itself. The research investigates the role of the digitally enabled technologies in modifying the disciplinary approaches to yacht design, a particular field of industrial design in which engineering and design approaches are mixed and overlapped. Through case studies and forecasting workshops, the research proposes a journey toward a more digitally conscious and virtually collaborative environment, highlighting as the traditional process of the yacht design discipline is no more valid. The research results, presented in the form of three roadmaps, show as 4.0 digital technologies are deeply transforming not only the representation of a design project but also its formal references and tools. For this reason, the three possible shifts in the yacht design practices are highlighted—input data are moving from analogic to digital reframing the focus from the measuring to inferring, the use of parametric and generative tools is shifting the “digital doing” from drafting to logic, digital twins are modifying the approach to communication media toward more collaborative strategies.