Cities are recognized to be the result of continuous exchanges. The circulation of urban planning ideas and practices is a well-known aspect of these interactions. However, during the last decades these processes have intensified, increasing the uncritical implementation of tools based on a false premise of taken-for-granted ‘best practices’. This situation is even more relevant in developing regions such as the Hispanic Caribbean, with a long and shared history regarding Spanish colonialism, the influence of external powers, and the transfer of foreign urban ideas. Due to this region’s increasing vulnerability and countless urban challenges, it is paramount that local city planning policies and frameworks are catered to the specific needs of the region. As a result, the research aim is to assess the extent to which contemporary urban planning policies in the three main cities of the Hispanic Caribbean: Santo Domingo, Havana, and San Juan are being shaped by external influences. Using a casebased cross-national comparative approach, the research methodology is threefold: the context; studying under which circumstances ideas have been transferred historically through a review of the cities’ planning and development histories, the object; identifying what is being transferred through a policy content analysis of contemporary national and city level planning policies, and the actors; exploring by whom and through which mechanisms ideas are being circulated. This information was then analysed and compared applying the policy transfer framework developed by Dolowitz & Marsh (2000). The research revealed that there’s still both voluntary and coercive transfer of urban policy ideas happening in the region. Influences from the United States, Europe and Latin America are still strong with an increasing role by international development aid agencies and supranational organizations. The continued study of these complex processes was recommended to recognize power asymmetries and ensure sustainable urban growth and development.