Originally Posted by MDtR-Chicago

Odds are, the IHG signup bonus will go farthest. You should be looking at an 80k signup (there's a thread on FT for it). That's likely enough for 3-5 nights in lower end properties. If you can hit pointbreaks, it can be far more. Plus it doesn't hurt to have platinum status; makes the stay easier when you have a little bit nicer of a room.

The Marriott card could easily get you 4-5 nights in low-end properties in the USA but in your destinations, there tend to be fewer options, so it would probably look more like 2-3 nights.

Best bet would be to go look at the exact destinations you want and see what point totals are needed.