Climate change and sea level rise are phenomena with significant cultural dimensions at all spatial levels; however, these dimensions are often neglected in adaptation planning. The community and regional planning field is awakening to the importance of culture as a concern in planning, including community well being, distinctiveness, cohesion, and capacity. Since planning is often conducted with a spatial focus, the concept of cultural landscapes is a potentially useful tool, and in particular for climate change and sea level rise adaptation. This article describes an action research project for local sea level rise adaptation planning that attended to cultural landscapes. The planning process asked: (1) What core cultural landscapes are important to maintain? (2) What cultural landscapes may be lost due to external changes and adaptation choices? and (3) What cultural landscape adaptive capacities exist to achieve community resilience? The project communities are the towns of Yankeetown and Inglis, neighboring small towns situated in the rural Gulf coast of Florida. The project found that locally significant cultural landscapes emerge when residents participate in planning processes, and that these landscapes hold new keys to successful adaptation.