I'm working in Port of Spain right now (live in NYC) and have $1500 to spend on travel each weekend... to anywhere. I've seen enough Caribbean for now, so I was hoping some of you experts have some awesome ideas up your sleeve.

Rules:
Must be the weekend of 12/2/11 or 12/9/11
My flight cannot leave POS before 5pm Thursday
My flight must return to POS by 7am Monday
I don't want to spend more than $300 of my own money

Helpful for hotels:
I have 40k SPG points and 60k+ Hyatt points (just started consulting, so I'm not rolling in it yet).

Mileage Mavens, give me your best shot. I don't care about being on a plane almost all weekend so long as I take some awesome pictures for a few amazing hours. I promise to upload pics of the best destination if I make it!