My goal is to learn the history of Hilton Head Island and logically reason out the way it grew, marking Sea Pine’s design influence over time and place. This paper is meant to be a piece of nature and history writing, which has implications for the study of environmental economics and real-estate design practices, but is not strictly about either. The thrust of this piece is the mapping of developmental philosophies and their reflection in the land. This topic interests me because at its core, it looks at how decisions are made, and the trade offs that influence them. The paper is also about the formation of ideas that explore sustainable forms of human-environment interaction, but which do not give up the high quality of life that modern man has come to expect. Environmental issues will continue to influence social, economic and political thought as we move towards midcentury. Sea Pines champions a blending of man and nature that may be able to provide alternative and more efficient solutions to the problems that our society faces.