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Almost any time is a good time to visit, with temperatures consistently hovering between the mid-70s and 80s. “Peak” season is considered to be from mid-December to mid-April, when everyone up north wants to visit warmer climates.This is also considered the "dry season". During this time hotel rates are very high. Accommodations and rental vehicles can be hard to come by. Definitely book a few months ahead if you plan to come during the peak season. During the “off” season, from mid-April through mid-December, hotel rates are drastically reduced and fewer crowds make for a much more relaxing vacation.
Hurricane season runs from June 1 until November 30. Historically, peak Tropical Weather activity for this part of the Caribbean is September 10. When traveling here from mid-August through mid-October be aware that strong Tropical Waves, or worse may threaten. It does not take a Hurricane to make your stay a soggy mess. A good website to monitor weather here is the Weather Underground where Dr. Jeff Masters (a visitor to Vieques) maintains a valuable blog on Tropical Weather. Just type in zip code 00765 in the search box on the home page to pull up Vieques weather.