The circulation in a shallow lagoon–inlet–coastal ocean system is significant to material transports (e.g., debris, pollutants, and larvae). To study surface flows in this system, we deployed 35 surface drifters at various tidal phases and wind conditions during 2017 and 2018 in the Maryland Coastal Bays system (MCBs). Given that winds and tides are two important drivers of estuarine and coastal circulation, their influences on surface drifter trajectories were analyzed. Observations indicate that surface drifters exit (enter) the lagoon mostly during ebb (flood) currents, and clockwise circular movements at a length scale of 1.5 km formed at the outer edge of Ocean City Inlet (OCI). Under weak wind conditions, tides are primarily responsible for drifter movements near OCI, whereas both the long-fetch winds and tides are important near the relatively larger Chincoteague Inlet and backbays. Under strong wind conditions, surface drifter movements generally follow wind directions. In the shallow lagoonal system, relative effects of winds on surface drifters gradually become stronger in the regions further away from the adjacent inlet as tides are weaker. Further investigations indicate that the fastest and slowest surface drifters are near the small OCI and backbays with the weakened tides, respectively. The direct surface drifter observations that cover a wide spatial range and long time series can provide strong support to surface current simulations. Enhanced understanding of coastal physical oceanography in the MCBs can be beneficial to similar systems and coastal ocean communities.