This paper explores the use of an enhanced AFM-NSOM system tip as a nanoscale polarimeter. The tip consists of a tungsten-silicon conical photodetector modified with four differently-shaped subwavelength apertures, which enable the determination of incident light's four Stokes parameters and in turn its polarization state on the Poincaré sphere. The system is mounted on a standard Atomic Force Microscope (AFM) cantilever and can serve as a triple-mode scanning system, with complementary topography scanning, optical data analysis, and polarization state detection. The device was designed and simulated using the Comsol Multi-Physics software package, and initial steps toward fabrication were taken using the application of advanced nanotechnology tools to a commercial AFM probe. After a discussion of the advantages and drawbacks of drilled scanning tips vis-a-vis standard ones, the article presents the simulation and fabrication results of the nano-polarimeter tip.