People have redesigned coastlines, creating ports, shaping waterfronts, and building cities to connect water and land. Specialists from many disciplines have explored the function and design of the water–land transition over many centuries. Among them is planning, a discipline that engages both with the functionality of working ports and the design of the waterfront for the urban public. In order to explore the development of working ports and the revitalization of abandoned inner-city waterfronts since the 1960s, this paper reviews planning and planning history literature in regard to the specific appreciation of water. It first examines the planning of ports and its focus on improving the speed, safety, and logistics, assigning water an industrial role. Second, it reflects on the design of post-industrial waterfront spaces, which ascribes a more aesthetic and symbolic as well as leisure-related role to water. Third, it points to the recent reconnection of cruise shipping with inner-city waterfront redevelopment and the coastline in general. In conclusion, the paper underscores localized perceptions of water in planning literature and the need to recognize how interconnected water systems connect otherwise separated areas along the same coastline. It argues for the integrated planning of port, waterfront, and city in conjunction with a comprehensive study of the environmental and ecological role of water in each of those places, both as a resource they share and, with climate change, a risk to which they must collectively respond.