A serendipitous meeting on board a week-long art-science expedition, sailing around the Outer Hebrides in Scotland, led to four art-science collaborations between the authors—socially engaged visual artist Stephen Hurrel and creatively inclined marine social scientist Ruth Brennan. Our initial collaboration was sparked by the realisation that our scientific and artistic practices overlapped, both methodologically and practically. The richness of our collaborative process and the responses to our work encouraged us to continue our cultural mapping of the emotional and socio-cultural values of diverse marine environments over the course of five years. It became clear that there was a need for new creative approaches to articulate these values and to understand how different ways of knowing can inform marine planning and management. This chapter goes behind the scenes of three of these collaborations, drawing from our notebooks from 2011 to 2015. We provide insights into the participatory and creative practices we used to engage with small island and coastal communities as well as the challenges faced throughout our collaborative process.