Eddi et al. [Phys. Rev Lett. 102, 240401 (2009)] presented experimental results demonstrating the unpredictable tunneling of a classical wave-particle association as may arise when a droplet walking across the surface of a vibrating fluid bath approaches a submerged barrier. We here present a theoretical model that captures the influence of bottom topography on this wave-particle association and so enables us to investigate its interaction with barriers. The coupled wave-droplet dynamics results in unpredictable tunneling events. As reported in the experiments by Eddi et al. and as is the case in quantum tunneling [Gamow, Nature (London) 122, 805 (1928)], the predicted tunneling probability decreases exponentially with increasing barrier width. In the parameter regimes examined, tunneling between two cavities suggests an underlying stationary ergodic process for the droplet's position.