A semiclassical method is used to study Landau damping of transverse pseudo-spin waves in harmonically trapped ultracold gases in the collisionless Boltzmann limit. In this approach, the time evolution of a spin is calculated numerically as it travels in a classical orbit through a spatially dependent mean field. This method reproduces the Landau damping results for spin-waves in unbounded systems obtained with a dielectric formalism. In trapped systems, the simulations indicate that Landan damping occurs for a given spin-wave mode because of resonant phase space trajectories in which spins are "kicked out" of the mode (in spin space). A perturbative analysis of the resonant and nearly resonant trajectories gives the Landau damping rate, which is calculated for the dipole and quadrupole modes as a function of the interaction strength. The results are compared to a numerical solution of the kinetic equation by Nikuni et al.