Maritime tourism has become a competitive opportunity for many island destinations in search of sustainable development. This article aims to analyze the hypothesis that tourist satisfaction with nautical destinations depends on the experience of previous visits to competing destinations. This hypothesis is relevant in order to ascertain the extent of potential coopetition between tourist destinations from the point of view of the consumers. This may ask for the need of cooperation within the competitive environment in which tourist destinations manage sustainability. The evidence is obtained from the case of Cape Verde, an archipelago strongly committed to the development of the nautical sector. Survey data from nautical tourists’ satisfaction visiting Cape Verde is modeled utilizing an ordinal logistic approach. Results show that tourist satisfaction with Cape Verde increases with the authenticity of the cultural experience offered by the destination, the diversity and quality of the nautical offer and the security perceived. Moreover, tourists declaring a satisfactory travel experience in other recently visited islands have higher levels of satisfaction with the nautical destination of Cape Verde. This suggests that proper strategies for nautical tourism development in these islands should not only allow tourists to discover the best cultural and local values of the destination, but also enhance their awareness of the quality of the experience provided by island competitors and, therefore establishing a benchmark for the common benefit of all island destinations becomes of interest. In this regard, coopetition strategies among islands with common interests of specialization may allow them to gain better positioning in the international nautical tourism market, and contribute to tourism development and the sustainability of the industry.