budget? circumstances? have plenty of faves and some i cant wait to experience. if you're in NY. Bermuda is nice; easy to get to Paradise Island as well as the Yucatan, Grand Cayman, Jamaica maaan, St Maartin (french side) or St Thomas (my fave is St John) and even the southern Caribbean (too many fun spots to mention). Sagaponnac and Martha's Vinyard are in your back yard for driving.
I'm 13 and just for back from my 12th visit to Europe. If you don't mind the cost of airline tickets go to Europe. Germany is gorgeous Italy is breathtaking and Spain is fantastic. I would tour these or just pick some pretty town in one and chill there. You won't regret it.
Most people would head straight to Mexico because it is cheap due to the bad rep they are having right now. However, I'd have to say that Cuba and Dominican Republic are gaining popularity just because it's nice down there and relatively cheap. If you have a tight budget, those would be the logical choices.