Nearctic Neotropical migratory songbirds incur the highest mortality during migration. En-route, songbirds rely on a network of stopover sites to rest, refuel, and/or seek refuge during poor weather. Conservation strategies prioritize protection of sites that best meet these needs. However, the specific function of a stopover site is expected to vary in relation to factors, such as geographic location, surrounding landscape, and weather. To identify sites with the highest conservation value for migratory songbirds, a conceptual framework was independently developed to classify sites into three functional categories based on their geographic and landscape features: fire escapes, convenience stores, and full-service hotels. The few attempts to empirically validate this framework have focused on temperate stopover sites. We evaluated the framework by testing the hypothesis that a site’s geographic and landscape characteristics can predict its function. We used capture and radio-tracking data at an island and mainland site in the Yucatan Peninsula, Mexico to quantify mean and variance in daily capture rate, body condition, stopover duration, and departure behavior during autumn, with a focus on four species: Swainson’s Thrush (Catharus ustulatus), Red-eyed Vireo (Vireo olivaceus), Gray Catbird (Dumetella carolinensis), and Prothonotary Warbler (Protonotaria citrea). Our results supported our predictions that the island functions as a fire escape, providing refuge for very high numbers of birds after encountering crosswinds or headwinds over the Gulf of Mexico, and the mainland forest site serves as a full-service hotel. The framework provides valuable insight for strategic conservation planning and management of stopover sites for songbirds. We suggest future studies evaluate the framework’s application to non-forest bird species. Additionally, we encourage collaborative efforts to consolidate and integrate tracking data, capture data from migration banding stations, and radar-based bird density estimates across a broad geography to test the framework’s ability to inform conservation planning across species’ full migratory range.