In this paper, we develop exploratory research to improve the understanding of actual practices applied in the port industry relating to local communities’ perception measurement and public engagement, aiming at maintaining and fostering relationships with local communities. The application of such practices would allow port managing bodies to improve their strategic alignment with the needs and requirements of their local communities. To this end, we distributed a survey to North American port managing bodies and terminal operators. The survey, answered by 37 respondents, follows a structure defined by critical elements affecting stakeholder perceptions and acceptability in relation to a project or an ongoing business activity. The results disclose differences in social license to operate measurement and public engagement practices between port managing bodies and terminal operators. Furthermore, follow-up interviews were conducted with eight port managing bodies in order to capture the value added and the barriers to engage with local communities. Finally, the study enables benchmarking possibilities both within the sample and on a global level, giving an indication and assessment of the respondents’ competitive positions regarding stakeholder perceptions, communication, and engagement practices, and the steps to be taken in order to strengthen any strategic and competitive state.