In this work, various aspects concerning the numerical simulation of a sailing boat are investigated. The attention is focused on simulation of the free-surface, the fluid-structure interaction (FSI) between wind and sails, and the dynamics of the whole boat. Some preliminary work on shape optimization is also presented. Free-surface simulations are carried out both on classical academic benchmark problems and for the prediction of the wave pattern around racing yachts. The comparison with experimental results and numerical data obtained with other CFD codes has proven the validity of the proposed set-up. In this framework, the Level Set method has been implemented and validated as a possible solution to the problem of interface diffusion arising in planing conditions with the standard Volume of Fluid approach. The FSI problem governing the interaction between wind and sails is solved via a strongly coupled segregated approach based on the standard Dirichlet-Neumann coupling. The structural solution is based on a MITC4 finite-element shell code. The fluid and structural meshes are non-conforming and the exchange of information at the interface is obtained via radial basis functions (RBF) interpolation. The fluid mesh motion is accomplished either through the mapping generated using the radial basis functions or via a method based on the inverse distance weighting (IDW) interpolations. The attention is paid to the methodological aspects of this complex problem and to the analysis of the numerical results. The fluid-structure interaction simulations of one and two sail configurations, with different trimmings, are presented; both steady and transient simulations are performed. The results obtained are very encouraging and show the potential of the proposed model. The dynamic motion of the Series 60 hull and the Alinghi’s AC 32 monohull complete of bulb, keel and sails have also been investigated. For the latter in particular, the free sink, trim and roll case has proven to be particularly interesting, with the boat rolling considerably on the side due to the aerodynamic loads exerted by the wind on the sails. Here, the whole boat has been considered as a rigid body but the integration of the FSI module for the sails into the full boat dynamic system is already under development. Finally, a preliminary analysis of shape optimization techniques applied to sailing boat elements have been investigated: in particular the attention has been focused on the drag minimization of (pseudo) bulb geometries under the constraint of fixed volume/fixed righting moment. The shape parametrization have been achieved either using directly the surface element nodes or via the Free Form Deformation (FFD) technique while the optimization algorithm has been based either on the solution of the adjoint Navier-Stokes equations or via pseudo finite-difference algorithms. The algorithm and developments mentioned have been implemented in a common open-source framework, the library OpenFOAM®.