This paper investigates the use of meta-models for optimizing sails trimming. A Gaussian process is used to robustly approximate the dependence of the performance with the trimming parameters to be optimized. The Gaussian process construction uses a limited number of performance observations at carefully selected trimming points, potentially enabling the optimization of complex sail systems with multiple trimming parameters. We test the optimization procedure on the (two parameters) trimming of a scaled IMOCA mainsail in upwind conditions. To assess the robustness of the Gaussian process approach, in particular its sensitivity to error and noise in the performance estimation, we contrast the direct optimization of the physical system with the optimization of its numerical model. For the physical system, the optimization procedure was fed with wind tunnel measurements , while the numerical modeling relied on a fully non-linear Fluid-Structure Interaction solver. The results show a correct agreement of the optimized trimming parameters for the physical and numerical models, despite the inherent errors in the numerical model and the measurement uncertainties. In addition, the number of performance estimations was found to be affordable and comparable in the two cases, demonstrating the effectiveness of the approach.