The harvesting of wind energy and its transformation into a thrust force for ship propulsion are gaining in popularity due to the expected benefit in fuel consumption and emission reductions. To exploit these benefits, a proper matching between the conventional diesel engine-screw propeller propulsion plant and the wind-assisted plant is key. This paper aims to present a method and a code for the preliminary sizing of a ship propulsion plant based on a diesel engine, a controllable pitch propeller, and one or more Flettner rotors. A mathematical model describing the behaviour of the rotor in terms of propulsive thrust and power is proposed. The rotor model has been integrated into an existing diesel propulsion model in order to evaluate the ship’s fuel consumption. The ship’s propulsion model is written in a parametric form with respect to the following design parameters: ship dimensions and resistance-speed curve, propeller diameter, engine power, rotor geometry, and true wind conditions. The methodology helps in evaluating the engine–propeller working points and eventually the total ship propulsive power, including the power required to spin the rotor. It provides a way to compare wind-assisted propulsive solutions in terms of fuel consumption and CO2 emissions. A 3000-ton Ro-Ro/Pax ferry has been selected as a case study. Results on the parametric analysis of rotor dimensions and propeller pitch optimization are presented.