A variety of theoretical techniques, including Monte Carlo (MC), mean field theory, and spin-wave theory, are used to analyze the phase diagram of a system of planar rotors on a triangular lattice with vacancies. A simple anisotropic interaction, which mimics the electric quadrupole–quadrupole interaction for diatomic molecules confined to rotate in the plane of the surface, induces a herringbone-ordered structure for the pure (x = 1) system, whereas for x ≈ 0.75, if the vacancies are free to move, a 2 × 2 pinwheel structure is favored. For x = 0.75, MC calculations give a continuous transition with Ising exponents in agreement with renormalization group predictions for this universality class, the Heisenberg model with corner-type cubic anisotropy. Mean field theory gives the unexpected result that the pinwheel phase is stable only along the herringbone-disordered state coexistence line in the temperature versus chemical potential phase diagram. Spin-wave theory is used to show that there is, in fact, a finite domain of stability for the pinwheel phase, and a complete phase diagram, which encompasses all available information, is conjectured.