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Coastal regions have historically represented a significant challenge for air quality investigations because of water-land boundary transition characteristics and a paucity of measurements available over water. Prior studies have identified the formation of high levels of ozone over water bodies, such as the Chesapeake Bay, that can potentially recirculate back over land to significantly impact populated areas. Earth-observing satellites and forecast models face challenges in capturing the coastal transition zone where small-scale meteorological dynamics are complex and large changes in pollutants can occur on very short spatial and temporal scales. An observation strategy is presented to synchronously measure pollutants “over land” and “over water” to provide a more complete picture of chemical gradients across coastal boundaries for both the needs of state and local environmental management and new remote sensing platforms. Intensive vertical profile information from ozone lidar systems and ozonesondes, obtained at two main sites, one over land and the other over water, are complemented by remote sensing and in situ observations of air quality from ground-based, airborne (both personned and unpersonned), and shipborne platforms. These observations, coupled with reliable chemical transport simulations, such as the National Oceanic and Atmospheric Administration (NOAA) National Air Quality Forecast Capability (NAQFC), are expected to lead to a more fully characterized and complete land–water interaction observing system that can be used to assess future geostationary air quality instruments, such as the National Aeronautics and Space Administration (NASA) Tropospheric Emissions: Monitoring of Pollution (TEMPO), and current low-Earth-orbiting satellites, such as the European Space Agency’s Sentinel-5 Precursor (S5-P) with its Tropospheric Monitoring Instrument (TROPOMI).