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Am I to presume you are flying from Europe, not North America?
Dominican Republic is an excellent choice on the way back.
Have you got unlimited cash? I'm sure each of the destinations you mention have different fares. I've been to all three.
If you are looking for a beach holiday ringed by casinos and tourists, Aruba is the place. It is also very close to Venezuela with a flight via Curacao. Trinidad is nice, but Tobago is fantastic. Very close to Venezuela, but I find only one flight, and quite expensive. Puerto Rico is to my mind the best of the bunch, though it is similar in many ways to Dominican Republic (which is much poorer). It's more expensive because it's the USA, and I don't see much in the way of flights from San Juan to Caracas.
If you are coming from Europe, why don't you try Cuba as a first stop?
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