Many small island destinations owe their spatial character to their entanglements with stakeholders involved in the arts. Space is the dynamic outcome of complex relational processes, which makes it impossible to identify a straightforward development path - including when it comes to the arts and tourism. Using assemblage thinking, we scrutinize the different translocal processes influencing art-based tourism activities on Bornholm, Denmark and Naoshima, Japan. On these islands, artists, investors, residents, destination managers, creative individuals, and government officials are all involved in networks and negotiations that form complex translocal assemblages of art and tourism. The craft-artists of Bornholm took advantage of regional development policies aimed at fostering rural tourism development, and subsequently established a destination known for quality professional craft art. On Naoshima, top-down corporate investments in large-scale art developments have clashed with local stakes in rural revitalization. These top-down projects have attracted creative in-migrants who have further turned Naoshima into a hybrid space. While Bornholm's entanglement with the arts stems from the possibilities generated by its spatial evolution, Naoshima's involvement with the arts first led to reterritorialization and then creative enhancement. Both islands are, thus, distinct loci of translocal art trajectories.