Migration can be costly with consequences that can influence population trajectories. These costs and consequences are especially heightened during over-water travels, which can be high-risk events for birds. We created spatial models to evaluate potential migratory responses of “oceanic”, island-hopping grey-faced buzzards that encounter variation in landscape parameters and weather as they move through and out of the Philippine archipelago. We constrained the modeled routes to enter the island chain at Basco and to use one of four potential exit points in the south of the country, either Balabac, Bongao, Balut Island, or Cape San Agustin. We used all possible combinations of our three external parameters (stopover sites, water crossings and wind direction) to model alternative migratory routes for each of the four exit points (n = 20 migratory routes). Modeled grey-faced buzzard routes were between 1,582 and 2,970 km. Routes overlapped over eastern and central Luzon, along a leading line created by the Sierra Madre Mountains. Routes also overlapped and suggested unavoidable over-water crossings between Mindoro and Palawan, Negros and Zamboanga del Norte, and Leyte and Surigao. Our models suggest that the optimal migratory strategy for these birds is to find the shortest route to an exit point with the greatest possible access to stopover habitats and fewest open-water crossings under wind resistance. Understanding how each of these external factors affected the geography and characteristics of the migratory routes helps us to understand the context for different migratory strategies of birds that face dangerous open-water crossings on migration.