When designing a hull that needs to account for sails, either rigid or flexible, it is necessary to consider the larger leeway and heel angles deriving from the sails side-forces compared to a traditional ship. It is therefore necessary to explore the possibility of adding appendages to the hull to balance those forces, achieving an optimum trade-off between hydrodynamic efficiency and manoeuvrability. The possibility of numerically simulating the manoeuvre coefficients at design stage will increase the chances of understanding the behaviour of a ship from an early stage in the design process. The current research is based on the evaluation of hydrodynamic efficiency and manoeuvre coefficients of a hull with rudders and shafts in a pure resistance, self-propulsion and in a wind-assisted mode. Having assessed the performances of the vessel with a Velocity Prediction Program (VPP), an in-depth research on suitable appendages was performed to reduce the experienced leeway angle, and ultimately increase the performances of a wind-assisted ship, especially when subject to wind angles ranging between 40 and 80. Many CFD simulations were initially performed to assess the hydrodynamic characteristics of the hull in a range of flow directions, rudder angles, ship speed and combinations. Those simulations encompass the whole range of datapoint needed to describe the forces and moments acting on a wind-assisted ship, simulating a towing-tank captive test, namely performing a Virtual Captive Test (VCT) [1]. Three types of possible appendages used to increase the generated side-force of the wind-assisted vessel are further investigated and the advantages and disadvantages are described. The findings of those preliminary simulations are then used as a basis for a structured model testing campaign.