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We've only been to Playa in November (the last 4 years) and always found it a great time to go, especially if you want to avoid crowds. In 2009 we went late October-early November. It was a bit hot for us (over 100F) and more humid with lots of mosquitoes. So be prepared for that. But this is also the time for Day of the Dead activities, and they do some fun stuff in town and out at Xcaret. We went late-November/early-Dec in 2008 but that was a little too cloudy for us. We generally now go mid-November when the weather is usually a little more to our liking--but there are no guarantees. We stopped by the Reina Rojo in 2010 mid-November and it was pretty dead, although they did have an apparently lively Miss Playa contest on their roof bar the previous weekend. Partying aside, going off-season has its advantages----no lines at Xplor, no reservations required for most excursions (like Rio Secreto), cheaper rates, etc. And 5th Avenue will always be lively at night.
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