The use of finite element method (FEM) tools is proposed to investigate the structural response of an ecosustainable sailing yacht to different loading conditions, typical of those acting during regattas. The boat is, in particular, a 4.60 m dinghy with the hull and the deck made of an hybrid flax-cork sandwich and internal reinforcements made of marine plywood. A preliminary activity has consisted in the refitting of an existing model in order to reduce the hull weight and to improve performances during manoeuvrings. These tasks have been interactively simulated in the virtual environment of the boat CAD model, where longitudinal and transversal reinforcements were enlightened and the maximum beam reduced. At the same time, results of FEM simulations on the modified model were analysed in order to verify the structural integrity. Shape modifications have been applied to the real model in laboratory and the resulting hull has been instrumented with strain gauges and tested under rigging conditions to validate the numerical procedure. Finally, the FEM model was used to predict the response of the boat to loading systems typical of sailing conditions.