This chapter explores transmedia storytelling in an attempt to contribute to the conceptualisation and definition of nautical tourism. The study employs a quantitative approach for the analysis of transmedia representations of nautical tourism and identifies the variables involved in the nautical tourism experience. The results demonstrate the need for re-defining nautical tourism in a sustainable and anthropocentric way. The inclusion of smaller scale practices, the onshore/coastal activities and the local human, cultural and natural environment seem to shape the nautical tourism ‘experiencescape’ that is presented and distributed online through multiple channels, digital travel communities and social media networks.