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As the Whale and dolphin Watching (WW) industry grows, so does the need for better industry management. The present study aims to both evaluate the current compliance of WW operators with local WW statutory tools, as well as gain a multi-perspective overview of WW activities in the Strait of Gibraltar. To this end, a total of 637 questionnaires were filled out by stakeholders including WW customers and operators, researchers, environ­ mental NGOs, technicians, and policy makers in Tarifa and Gibraltar between 2017 and 2019. A direct assess­ment of WW activities was also carried out in 2019. Results suggest that (1) local operators only partially follow rules, (2) customers prefer, and give higher ratings to operators when cetaceans are indifferent to or approach vessels and (3) stakeholders recognise the educational, scientific, and recreational values of WW. Suggestions for the improvement of compliance include the land-based monitoring of WW activities, the analysis of Automatic Identification System data and an increase in patrolling and enforcement (e.g., revoking of licenses). Moreover, the introduction of structured educational programmes during WW activities the designation of Marine Protected Areas, and of a regional shipping plan, together with an integrated management approach, could benefit the WW industry and improve its sustainability in the Strait.