Puerto Rico or Jamaica
 

My wife and I will be using some freq. flier miles to travel to the Caribbean for the first time this summer. We're planning on spending time in the DR (Casa de Campo in La Samana & Melia Caribe in Punta Cana) during the first portion of our trip and are trying to decide whether to end the trip w/ a few days in Jamaica or Puerto Rico. For those who are familiar w/ the region, which of these 2 islands do you prefer and why.

In terms of preferences, we enjoy exploring cultures/islands vs. hanging out in the hotel resort all day and was wondering what you would recommend based on past experience. Any feedback would be greatly appreciated. Thanks.

While I like both and prefer Jamaica, geographically you would be much better off going to PR. Going to DR and then Jamaica would require you flying to San Juan and then Miami and then Jamaica (or directly to Miami and then Jamaica). If you are flying AA - you can do a stop over in Puerto Rico without any additional points.