please
Budget?
Desired length of stay?
Do you care about time in transit, and if so, how much do you care?
Do you just want to bang and hang on the beach all day, or do stuff?
How much do you care about things like ethnic food and shopping?
Do you want to do something all inclusive? (or maybe a less rigid option like hotels with a meals+local beer/wine added kind of deal? Or neither...)
EDIT: Oh! Also, what time of year this will happen matters, too - hurricane seasons, typhoon seasons, monsoon seasons etc. I'd want to tailor my suggestions to places that have ideal weather during that time of year.
PM me if any of this is semi private.
I am the shit at helping people put together travel plans, I've acted as a casual travel agent for friends for years. I can suggest locations, hotels, places to eat, etc.