Knowing how naïve migrants respond to intrinsic and extrinsic factors experienced en route will allow a more thorough understanding of the endogenous migratory programme. To understand how inexperienced individuals respond to ecological features, we tracked the migratory departures of juvenile ruby-throated hummingbirds, Archilochus colubris, one of the smallest (∼ 3 g) and least-studied migrants, along the Gulf of Mexico during southbound migration using an international automated radiotelemetry system. The recent miniaturization of radiotags provides a novel method to track one of the smallest migratory birds, rendering the first information on departure decisions of known hummingbirds in relation to an ecological barrier. Using weather conditions and individual attributes, we also determined which factors influenced the time and direction of departure from a coastal stopover site. Most migrants (83%) departed in the morning, and daily departure time was only influenced by stopover duration, the amount of time spent at a stopover site. The majority (77%) of departure orientations paralleled the coastline, and we found little influence of any factor on departure direction. Our results reveal that (1) juvenile hummingbirds departing coastal Alabama move in a direction indicative of a circum-Gulf path during southbound migration and (2) departure decisions support a fly-and-forage strategy in which hummingbirds likely take advantage of resources along the coast while moving towards their destination.