re: Hawaii vs Caribbean Upscale Resort Trip

Been to both several times. If food is high up on the list, then Wailea in Maui would be my suggestion. You'll have a ton of restaurant choices with great beaches and everything else. Obviously Honolulu gives you a greater variety of restaurants, but it's not a quiet scene.

Most Caribbean resorts won't give you the quality or variety of food options. But, some of the locales can provide some decent options.