This paper investigates the contemporary issues in waterfront regeneration strategies. It evaluates and analyzes the legacies from past international waterfront projects through case examples and review policies, practices, trends and issues that pertain to waterfront regeneration. The impact of these within urban regeneration and urban cultural contexts are in turn considered. In this respect, the paper tracks the changes from typical festival-type market regeneration initiatives of the 1980s and 1990s to more culturally and entrepreneurial-focused projects evidenced today. Contemporary issues that stakeholders should consider when evaluating waterfront projects are considered. The paper gives recommendations for the direction of future waterfront development strategies. Conclusions promote the accommodation of more inclusive, socially responsible, culturally relevant, innovative, entrepreneurial and integrated regeneration objectives to ensure the future success of waterfront projects.