Dec. Weather
#2
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We usually take another vacation in December--normally to Jamaica, Antigua, St. Martin or Aruba and the weather has always been very good, in fact more pleasant than other times of the year. Rain is usually only for a short period of time if at all. We love the islands this time of year and it is less crowded other than the holiday period.
#4
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I can only speak for the Netherlands Antilles. We get some rain in December, but it comes in small spurts so it's not enough to "dampen" your vacation. However, this past December we had over a week of rain and bad weather, so you really can never tell.