The Great Elliptic Sailing (GES), which can reduce sailing distance, is important to navigators. Whether a Great Ellipse (GE) is worth using depends on whether the distance saved is significant. Otherwise, the Rhumb Line (RL) is easier to steer. We propose a simple criterion to evaluate the difference in distance between the GE and the RL. The criterion is that the GE is worth using when the vertex lies between the departure and destination. In order to take the advantage of shorter distance, the GE is usually approximated as a series of waypoints. Unlike currently practised methods, we propose the Longitude Bisection Method (LBM) which determines waypoints with varying intervals. This approach can establish the appropriate number of waypoints to approximate the GE effectively. The proposed criterion and the LBM are demonstrated in practical examples.