-hh
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During the winter months in the Caymans,the winds are more likely to be from the north, which can prevent you from getting to the better dive sites on the north side. On Little Cayman, the premier dive sites are in the Bloody Bay/Jackson Bay area to the north.
Exactly. This weather is caused by strong winter cold fronts over the USA, which is what delivers what Caymanians refer to as "NorWester" storms. To give you an idea as to how strong these can be, it was a NorWester that broke the #356 wreck in half - - it was NOT a hurricane as you usually hear claimed. If you want an indirect way of gaging the "winter" weather, go data mining on the Cayman Aggressor's website and plot what weeks they don't make the crossing from Grand Cayman over to Little Cayman...its roughly "Now through Easter" as the time of year.
Most of the hotels and dive ops are based on the south side, which has decent diving (at least for a couple of days), but it's hard to get the boats around to the northern sites when it's really blowing from the north. I'd aim for the May/June/July time frame to maximize your chances for good conditions.
I've gone to the Sister Islands in April, May, June, July, Sept, Oct, Nov, Dec.
I'd agree with the May-July timeframe, although with a caveat of it being late May and to also be aware of if you're allergic to thimble jellyfish, which IIRC usually hatch in the first half of this timeframe, and also with the caveat that the latter half (July) can be "stinking hot" on shore.
The July trip was probably one of the best for the diving, but it was simply too miserably hot topside to do again...the same low winds that made the water glass meant no relief topside. The April weeks were a northerly blowout, the May & June trips were fine but had thimble jellies (which don't bother me) and the Nov & Dec were fine. The Sept/Oct periods are when I've gone the most (36 weeks worth over the past 19 years; timeshare) and this was originally selected despite the hurricane risk because it is less crowded, flights cheaper, water still warm and air not too hot. Granted, I have had a few hurricane scares, but only 1 in 19 years, not including missing Ivan by dumb luck. This was Lily (2002), and while we lost two dive days from a direct hit from a CAT-I, our first day out diving after the storm, the conditions were already good enough for a run from the Brac to Little Cayman and we ended up having honest 200+ft visibility. Go figure.
Insofar as other time-of-year things, in the Aug/early Sept time period, you can expect some reduced visibility due to the annual coral spawning (~100ft), and algae on the reef will be thickest then, as its been growing all summer but hasn't been scrubbed off yet by a winter storm.
The reality is that any month has its trade-offs.
-hh