Pantala flavescens or the Globe Skimmer, a commonly available species of dragonfly, performs a fascinating multi-generational transoceanic migration between India and Africa (see Figure below). The intriguing annual migration was reported a century ago. The multi-generational, transoceanic migration circuit spanning 14000-18000 kms, from India to Africa is an astonishing feat for an insect few cms in size. Wind, precipitation, fuel, breeding, and the life cycle affect the migration, yet understanding of their collective role in the migration remains elusive. We identify the transoceanic migration route by imposing a time constraint emerging from energetics on Dijkstra’s path-planning algorithm. Energetics calculations reveal Pantala flavescens can endure 90 hours of steady flight at 4.5m/s. We incorporate active wind compensation in Dijkstra’s algorithm to compute the migration route from years 2002 to 2007. The prevailing winds play a pivotal role; a direct crossing of the Indian Ocean from Africa to India is feasible with the Somali Jet, whereas the return requires stopovers in Maldives and Seychelles. The migration timing, identified using monthly-successful trajectories, life cycle, and precipitation data, corroborates reported observations.Wind drift compensation is crucial for the dragonflies to reach their destination. We conducted tethered flight experiments in a wind tunnel on live specimens of P. flavescens. Specifically, we evaluated the tethered flight in the tailwind and headwind for different crosswind orientations by comparing the distribution of mean values of thrust, side force, and lift between the headwind and the tailwind. Further, we conducted high-speed Schlieren flow visualization to visualize two distinct flight modes and the associated vortical flow structures.