Epidemics of dengue, chikungunya, and Zika have been threatening the Caribbean. Since risk communication (RC) plays a fundamental role in preventing and controlling diseases understanding how RC works is essential for enabling risk-reducing behavior. This multimethod qualitative study compares news reports with local’s and health professional’s perspectives, currently lacking in RC research. It was found that RC strategies were obstructed by a lack of governmental structure, organization, and communication. The content analysis showed that the majority of newspaper articles contained negative reporting on the government. Furthermore, this study shows how trust and heuristics attenuate or amplify people’s risk perceptions and possibly positively and negatively influence people’s risk-reducing behavior. A transcending approach (e.g., structural, cooperative, and multidisciplinary) of the prevention and control of vector-borne diseases and the corresponding RC is recommended.