Surface enhanced Raman scattering (SERS) measurements have been carried out at different focusing conditions using objective lenses of different numerical apertures. The experimentally observed dependence of SERS intensity of thiophenol-coated Ag nano-islands shows a close-to-linear scaling with the collection aperture. The linear relationship breaks down for large numerical apertures, which suggests that the scattering is anisotropic. Numerical simulations of realistically shaped Ag nano-islands were carried out, and the spatial distribution of hot-spots has been revealed at different heights near the nano-islands. Local field enhancements of up to 100 times were estimated. The simulation also suggests an explanation for the anisotropy in the scattering observed for larger numerical aperture objectives. This appears to be due to a reduction in the local field enhancement as the electric field vector component in the plane of the shallow metal islands reduces at larger angles of incidence.