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Peurto Rico, is definately a nice place. I would suggest staying in the Radison in San Juan because it's a short walk to the beach plus, theres a nice pizza place right accross the street which is amazing... and the food is great too. Plus, theres a "rain" forest as the locals call it a short drive away.
There's hikes, watersports, touristy stuff.... I would recommend going to the Ben and Jerrys there, they have a triple caramel ice cream that it awesome. The historical buildings are alright.... people seem to like them.... I got a few pictures on me in some of the towers. There is a ton to do there. I don't know about Jamaica but my choice would be Peurto Rico. Plus I thought that the cabs were a lot cheaper than the other islands in the carribean that I've been to.
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