The study compared sustainable policies and practices of ports in four different continents and understand the dilemmas, challenges, and opportunities they face in attaining sustainable development. The study examined ports in the USA (Port of Long Beach), the Netherlands (Port of Rotterdam Authority), Australia (Sydney Ports Corporation), and South Africa (Transnet Limited). It found that while there is progress towards sustainable development, several practices deemed to be sustainable can be controversial and must be critically examined from the perspectives of different stakeholders. Lack of data to monitor environmental impacts, economic costs of implementing sustainable practices, and complexities of international, regional, and national regulations were identified as constraining factors. The study suggested that the sustainable development paradigm has gained momentum in the functioning, organization, and ethos of the case study ports. The study highlighted the need for geographically-targeted approaches to incentivize the adoption of sustainable practices.