The first direct detection of gravitational waves ( GW ) by the ground-based Advanced LIGO/Virgo interferometers is expected to occur within the next few years . These interferometers are designed to detect the mergers of compact object binaries composed of neutron stars and/or black holes to a fiducial distance of \sim 200 Mpc and a localization region of \sim 100 deg ^ { 2 } . To maximize the science gains from such GW detections it is essential to identify electromagnetic ( EM ) counterparts . Among the wide range of proposed counterparts , the most promising is optical/IR emission powered by the radioactive decay of r -process elements synthesized in the neutron-rich merger ejecta – a “ kilonova ” . Here we present detailed simulated observations that encompass a range of strategies for kilonova searches during GW follow-up . We utilize these simulations to assess both the detectability of kilonovae and our ability to distinguish them from a wide range of contaminating transients in the large GW localization regions . We find that if pre-existing deep template images for the GW localization region are available , then nightly observations to a depth of i \approx 24 mag and z \approx 23 mag are required to achieve a 95 % detection rate ; observations that commence within \sim 12 hours of trigger will also capture the kilonova peak and provide stronger constraints on the ejecta properties . We also find that kilonovae can be robustly separated from other known and hypothetical types of transients utilizing cuts on color ( i - z \gtrsim 0.3 mag ) and rise time ( t _ { { rise } } \lesssim 4 days ) . In the absence of a pre-existing template the observations must reach \sim 1 mag deeper to achieve the same kilonova detection rate , but robust rejection of contaminants can still be achieved . Motivated by the results of our simulations we discuss the expected performance of current and future wide-field telescopes in achieving these observational goals , and find that prior to LSST the Dark Energy Camera ( DECam ) on the Blanco 4-m telescope and Hyper Suprime-Cam ( HSC ) on the Subaru 8-m telescope offer the best kilonova discovery potential .