Ratnagiri, a small town on the western coast of Maharashtra, is an important urban settlement in the Konkan region. This article examines the town's uneven spatial and economic development by focusing on the fishing and tourism sectors, highlighting the historically generated and socially produced contradictions and contestations within and between them. It argues that the very instruments of spatial planning meant to address uneven development end up reinforcing and exacerbating existing spatio-social and political inequalities. It goes on to trace the processes by which spatial planning becomes an arena where regulations are bent and flouted by directly influencing local and state-level actors through a negotiated approach to planning.