Abstract <p>The rectilinear motion of a wheeled cart with a propeller on a horizontal plane in a wind flow directed along the motion is considered. Based on a quasi-steady approach, two mathematical models of the propeller’s aerodynamics are developed. The first model relies on experimental data on the aerodynamic characteristics of the propeller—thrust force and torque. Within this model, the existence of a stable stationary motion regime of the cart downwind at a speed exceeding the wind speed is demonstrated. To expand the scope of the research, a second model, in which the propeller blades are approximated by thin rectangular plates, is proposed. The existence of an attractive motion regime of the cart upwind, powered by the wind energy, is established. The experimental part of the study involves the creation of a demonstration cart prototype and a series of tests in an aerodynamic flow. The experimental results confirm the possibility of realizing the two theoretically predicted motion regimes.</p>