This thesis develops a personal method and approach for designing in a delicate context such as the Key West Historic District. This thesis is composed of two parts. The first part presents observations of Key West, focusing on the form of the physical environment. The observations make no pretense of being a scholarly analysis, sacrificing accuracy of detail for breadth of scope. It is a search for the essential elements of Key West and it is an attempt to understand the spirit of the place as manifested in its form. The second part presents a series of design exploration for a hypothetical hotel in the Key West historic district. The design projections explore issues of building for growth and change in a delicate context, and the limits of such a context as a reference for design, in the hope that the design may be more deeply rooted in its context. The presentation of the thesis is primarily in the form of images--photographs and drawings, maps and diagrams.