When is the best time to go to the Caribbean? And why?

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I tend to avoid the northern Caribbean dive locations in the winter months due to the frequency of cold fronts/Nortes in places like Cozumel and GC, and the colder water and air temps in the Bahamas, etc. Like KathyV, I like May and June for most places in the Caribbean, but will go far south to Bonaire and Curacao any time of the year.
Last 2 mid-Decembers in Coz were simply perfect!
 
Hurricane season, because if you aren't having a hurricane, the weather is the bomb. And if you are, it's still the bomb.
 
https://www.shearwater.com/products/swift/

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