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I would avoid the Eastern Caribbean in the summer time as it gets quite humid, and hot with thundestorms each day. The winter/spring time is nice but you will have a lot of ships there in port each day. The fall has less ships than in the Spring but you have higher chances of hurricanes.
I think I would go in the January/February/March time frame given the rise in Hurricanes over the past few years.
I love late November and early December. I do this for several reasons. No hurricanes. Most kids are in school and the best reason, the weather in the eastern Caribbean is very nice. Usually a good breeze and lower humidity.