Open clusters potentially provide an ideal environment for the search for transiting extrasolar planets since they feature a relatively large number of stars of the same known age and metallicity at the same distance. With this motivation, over a dozen open clusters are now being monitored by four different groups. We review the motivations and challenges for open cluster transit surveys for short-period giant planets. Our photometric monitoring survey (EXPLORE/OC) of Galactic southern open clusters was designed with the goals of maximizing the chance of finding and characterizing planets, and of providing for a statistically valuable astrophysical result in the case of no detections. We use the EXPLORE/OC data from two open clusters NGC 2660 and NGC 6208 to illustrate some of the largely unrecognized issues facing open cluster surveys including severe contamination by Galactic field stars ($>$ 80%) and relatively low number of cluster members for which high precision photometry can be obtained. We discuss how a careful selection of open cluster targets under a wide range of criteria such as cluster richness, observability, distance, and age can meet the challenges, maximizing chances to detect planet transits. In addition, we present the EXPLORE/OC observing strategy to optimize planet detection which includes high-cadence observing and continuously observing individual clusters rather than alternating between targets.
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