A series of workshops attended by representatives of municipal and federal government, as well as community organizations and academia led to the development of three positive visions of the future for the coastal, Caribbean city of San Juan, PR. Workshop outcomes were quantified and used to modify pixel transition rules in a series of cellular automata (CA) simulations trained on historical land cover imagery, producing spatially explicit land cover projections up to the year 2080. CA results are then used as input to high-resolution (1 km) Weather Research and Forecasting (WRF) model simulations to study how these changes impact urban temperatures and other local processes (e.g., sea breeze and heat fluxes). Simulations of the three envisioned scenarios, using bias-corrected Community Earth System Model (CESM1) RCP 8.5 data, are compared against results from a “business as usual” land cover scenario, highlighting modification of the urban heat island and sea breeze.