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Which island for first visit? April/May

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My husband and I are planning a trip to the Caribbean sometime in April or May of 2017 for our 10th anniversary. We have a budget of somewhere around 3500-4000 for the two of us, including airfare from Portland, Oregon. We are looking at a total trip length (including flights) of 7-8 days (so maybe 6-7 nights?).

Which island/area should we visit? I was originally looking at Groupon, which has a lot of deals in Cancun/Riviera Maya, the DR, and Jamaica. Almost all are all inclusive. I don't know if we need an all inclusive.

I'm having difficulting getting this to post from my phone, so I am going to try posting this and put my vacation criteria in the comments section.

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