Achieving economic, social, and environmental sustainability of urban transport is one of the great contemporary societal challenges. By tracing urban land-use and transport policies and technological change in transport over a 60-year period in a case study of Istanbul, the authors demonstrate the displacement of more sustainable modes of transport (ferry, walking, and public transport) for a more automobile-dependent metropolis with road bridges across the Istanbul Strait (Bosphorus Strait). This article describes the main features, history, and status of the Europe-Asia crossings in Istanbul, thus framing a discussion of sustainability issues. Its originality is a discussion of sustainability through the economic, social, and environmental impacts of Europe-Asia crossings based on both a historical perspective and future prospects in order to assess whether current policies are leading toward more sustainable outcomes. The article concludes by emphasizing the impacts of policy decisions on transport infrastructures and highlighting some suggestions for policymakers.