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I'm going to Mexico for half of sept. It's the rainy season, but I will be on the Pacific side so it shouldn't be a problem.(falls in short bursts, usually at night). October has even less precipitations. November is even better.
I don't think that Caribbeans has good weather this time of the year though... you might want to double check that. If the weather is good, i know you can rent a jeep and cruise around Dominican Republic. Met someone who did that before. I wouldn't go to Jamaica myself... I just have no Interest to go there. My picks would probably be Mexico in second place and Costa Rica in first.
I book my tickets online and a place was rented by someone who already been there.
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