This paper presents an iterative learning approach for optimizing waypoints in repetitive path following applications. Our proposed algorithm consists of two key features: First, a recursive least squares fit is used to construct an estimate of the behavior of the performance index. Secondly, an iteration-to-iteration waypoint adaptation law is used to update waypoints in the direction of optimal performance. This waypoint update law parallels the mathematical structure of a traditional iterative learning control (ILC) update but replaces the tracking error term with an error between the present and estimated optimal waypoint sequences. The proposed methodology is applied to the crosswind path optimization of an airborne wind energy (AWE) system, where the goal is to maximize the average power output over a figure-8 path. In validating the tools from this work, we introduce a simplified 2-dimensional analog to the more complex 3-dimensional AWE system, which distills the problem to its core elements. Using this model, we demonstrate that the proposed waypoint adaptation strategy successfully achieves convergence to near-optimal figure-8 paths for a variety of initial conditions.