Underwater gliders have advantages for typhoon observation. In recent years, the typhoon resistance and cluster networking capabilities of such platforms have improved greatly; therefore, underwater gliders have received increasing attention for typhoon observation, no matter observing the salinity, density or temperature of the seawater during the typhoon. However, there is a lack of scientific evaluation of the sampling layout and planning of underwater gliders during tropical cyclones (TCs). Based on the simulation results of the three-dimensional Price–Weller–Pinkel numerical model (3DPWP) for Typhoon Hato, this study considers the working characteristics of underwater gliders to model the sampling results and proposes the first method of evaluate the simulated typhoon observation effect of underwater gliders. Subsequently, four kinds of heading schemes for an underwater glider array are designed and evaluated, and the optimal design of a glider array for typhoon observation, that is, the “along-typhoon parallel” mode, is identified through comparison. Finally, the optimal design employing a genetic algorithm is applied to Typhoon Hato to verify its universality and effectiveness. Underwater gliders with the best typhoon observation scheme are helpful to more completely observing and reconstructing the 3D structure of the tropical-cyclone-induced ocean response with greater precision.