Where is a good place to dive during the winter time that gives you the best chance of good conditions with the least amount of weather concerns?
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Assuming you're asking about the Caribbean....
The later in the "winter" that you delay your trip and the further South in the Caribbean basin that you go~ that's your best shot.
The ABC Islands, in example, and then a line drawn WNW to the Bay Islands and then Belize are pretty good bets.
It's nice to be optimistic, but realistically - have backup plans for blow out days. Keep your jacket handy too. I got chilled on Roatan one day in February.I'm counting on Cozumel this winter......