Damselfish
Contributor
I know you said you like the Caribbean, but sometimes flying there from the western US can be a pain schedule-wise. The couple hour time difference is enough to make connections to some places difficult and can result in unwanted overnights. Down the road you might want to consider checking out the Pacific, especially if you have more than a week. Sure it's a long flight, but airfares also often have little to do with distance. For example you can catch Philippines Airlines offering great sale fares from the west coast, I've periodically seen ~$750 from LAX to Manila or Cebu. While that flight is long, overall travel time can be less. Once you get there it's cheap, even for fairly nice places. No shortage of local culture and mostly way better diving than the Caribbean. Something to think about. Thailand is another place that could be inexpensive, though I'm unfamiliar with airfares to there.