Prey resources in oligotrophic tropical marine environments are often scattered and unpredictable. Tracking studies of tropical seabirds can provide critical information about ocean habitat affinities, prey choice and the utilisation of surrounding areas, which can be useful for conservation managers. Foraging studies of Red-billed Tropicbird populations in the Caribbean are scarce but increasing. We sought to expand on this by tracking chick-rearing adults using GPS devices and subsequently linking these tracking data to remotely-sensed environmental variables. We related our spatial data to opportunistic sampling of regurgitates in a globally significant nesting colony on Saba, Caribbean Netherlands. Diet samples were dominated by flying fish (Exocoetidae; numerical frequency: 70.73%), but prey items from the squid family (Loliginidae; 9.76%) and the families of flying gurnards (Dactylopteridae; 2.44%) and the ray-finned fish (Carangidae; 2.44%) were also identified, although we were unable to identify 14.63% of samples due to digestion. An additional goal of our study was to compare the foraging ecology of Tropicbirds on Saba with those nesting on St. Eustatius, located circa 25 km south-east. As expected, Tropicbirds nesting on Saba exhibited diurnal foraging patterns, travelling a maximum distance from the colony of 553.7 km, with an average trip length of 117.2 ± 144.6 km (±SD). Adults foraged in shallower, cooler waters with higher chlorophyll a concentrations and higher Exocoetidae species richness compared to travelling points. Despite the proximity of Saba and St. Eustatius, this is contrary to what was found for Tropicbirds nesting on St. Eustatius, where adults foraged in deeper waters with a low Exocoetidae species richness. However, Tropicbirds from Saba and St. Eustatius did exhibit some similarities in their foraging behaviour; specifically, foraging adults traversed multiple exclusive economic zones and marine protected areas, reinforcing our recommendation for nature managers in the Caribbean to create a transboundary network in order to effectively protect and conserve this species.