Originally Posted by
kooju999
Our dates are kind of flexible since my son's winter breaks is Dec 22,2012 - Jan 5,2013
Travailen said it best when he recommended SJU as a destination. My hometown. Not to be favorites, but what exactly you are looking for? I mean, they all have beach, great golf, scenery, etc. However, while you mention that your dates are flexible, you are still traveling during PEAK time, x-mas is one of the more expensive times of year to visit the Caribbean, airfare and accommodations are high during that time. If I'm correct, AA only has one direct Caribbean flight, to SJU, all other flights, to other Caribbean destinations will involve a connection in MIA.
SJU will probably be the best bet, no customs, lots of flight options, and also offers the possibility to do some day trips to other islands. I suggest you check the travel section tab on this board and look at Caribbean, there are numerous post in there. You can also go to your local library and pick some Caribbean destination books, read it over the weekend and see what areas appeal to you. Cayman Island are nice also, also the Dominican Republic, St Thomas, St Marteen.
Happy travels and enjoy.