Frequent travelers I need recommendation for fall traveling

[kicksgetmehigh]

I was supposed to go on a trip tomorrow but some medical issues came up, so I have to push my trip back. However... I was going with someone else and we want to go somewhere else. I'm currently working with $2k... what would you frequent travelers recommend? Some place where the USD is pretty strong, and has warm weather towards the end of the year. I'm gonna be with a chick who already gave me her half to pick a place.
I'm just out of options