Re: Jamaica
June or July you will be fine. I was there last summer the second week of July and I had the same concerns but really hurrican season hasn't kicked in yet at that point. It is what they call "rainy season" so the sunsets aren't the best in the world but I have some of the best sunsets here, so no biggie.
We went to Negril and stayed at Rockhouse. It isn't all inclusive if that is what you're looking for but I would highly recommend it. In fact, at some point I will no doubt stay there again.
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