I'm going to Mexico in 2 weeks, but on the Atlantic Side. Try to avoid the Caribbeans(remember the hurricane last week or so?). Also, there will be less rain starting in October. September is like the most rainy month.
I personally like the month of February to go down to the islands. It's far enough into winter to really escape the cold and snow, but also close enough to spring to make the look ahead not so tough.
It's funny you should mention that I was browsing on www.redtag.ca and was shocked to see how cheap it is to travel to the Caribean this time of year (Of course if you're not concerned about the rainy season) Personally if I could take the time off I would go.
Good time to go the caribean?
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