Despite extensive studies of hydrodynamics and sediment flux along beaches, there is little information on the processes, pathways and timing of water and sediment transport around rocky headlands. In this study, headlands along the California coast are classified to advance understanding of headland dynamics and littoral cell boundaries in support of improved coastal management decisions. Geomorphological parameters for 78 headlands were quantified from geological maps, remote-sensing imagery, navigational charts, and shoreline geospatial databases. K-means cluster analysis grouped the headlands into eight distinct classes based on headland perimeter, bathymetric slope ratio, and the headland apex angle. Wave data were used to investigate the potential for sediment transport around the headland types and determine the efficacy of the headland as a littoral cell boundary. Four classes of headland appear to function well as littoral cell boundaries, with headland size (e.g., perimeter or area) and a marked change in nearshore bathymetry across the headland being relevant attributes. About half of the traditional California littoral cell boundaries align with headland classes that are expected to perform poorly in blocking alongshore sediment transport, calling into question these boundaries. Better definition of these littoral cell boundaries is important for regional sediment management decisions.