This research proposes a numerical methodology to assess the behavior of a car towing a generic caravan in crosswind conditions. Driving with crosswind can lead to dangerous situations. The vehicle can have stability issues and eventually crash. Different crosswind and vehicle velocities have been analysed using a car-caravan dynamic model with accurate aerodynamic loads. The forces generated by the action of the wind are calculated with CFD simulations and applied to the vehicle to perform dynamic simulations. Results show that also non-extreme crosswind condition could lead to dangerous situations.