The small Caribbean republic of Trinidad and Tobago and the much larger southeast Asian republic of the Philippines shared colonial rule first by Spain and then by a major English-speaking power (the United Kingdom, in the case of Trinidad & Tobago, and the United States, in the case of the Philippines). Recent years have seen a distinct resurgence in interest towards the Spanish language and culture in the two island nations. Applying a cyclical five-stage language policy framework, this comparative exploratory analysis foregrounds the political, educational, and sociocultural developments regarding Spanish as a foreign language through the prism of the model’s stages of language policy emergence, agenda setting, formulation, implementation, and evaluation. This is achieved through desk-based analysis, thereby enabling a deeper understanding of the policy-related factors underpinning approaches to Spanish in the two case studies, whilst also noting the importance of relevant geopolitical factors. Finally, further suggestions are given to expand the scope of the analysis in the future. The model applied could be extended to include other Caribbean and southeast Asian countries, thereby enriching wider discussions on policies relating to the role and status of Spanish in the regional and international contexts.