Easy (short travel time) Warm Jan getaway from NY

[NYplayer]

I would like to go somewhere warm in January for 3 or 4 days with the wife. I live in New York and want it to be an easy trip so the caribbean is probably the best bet. Puerto Rico seems like it should be good because it's a direct flight. you have to change over for most of the other islands. We are just going to sit by the pool most of the time so the biggest concern is nice pool area with shade. i'm willing to spend up to $1,000 a night. Anyone have any suggestions of places they really like? My heart isn't set on puerto rico so if you have any other ideas i'm all for them.

[RoundGuy]

I think this is why we now have a Travel Forum.