A new concept for achieving high-altitude, long-endurance (HALE) flight is proposed and evaluated, which features two unmanned aerial vehicles (UAVs) connected via a long tether which effectively sail backand-forth using stratospheric wind velocity gradients. The potential of a baseline configuration to stationkeep (i.e., stay within a prescribed radius above a specific ground site) based on measured steady wind profiles is predicted analytically based on yearly sets of bi-daily wind profiles, and using a constrained optimization technique. The sensitivity of system operability to key configuration parameters (i.e., tether diameter, geometric scale, and wing loading) is evaluated.