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A freely rotating main sail, controlled by a tail rudder, and a directly actuated front sail enhance thrust and aerodynamic stability. A biomimetic caudal fin\u2013inspired rudder enables propulsion during low-wind conditions and agile maneuvering in challenging upwind tacking. We empirically evaluated different wingsail airfoils through wind tunnel testing and optimized rudder design through hydrodynamic modeling, material selection, and speed-power efficiency analysis across different sizes and stiffnesses. Field experiments validate aerial deployment from 150 meters, autorotating descent, passive self-righting, and successful waypoint navigation using both rule-based control and a reinforcement learning approach. 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