wateraddiction
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I agree that advance planning is key (and a little OCD don't hurt). I've been avoiding awards for CZM due to high taxes ($136/pp) compared to Bonaire or Roatan ($79 pp) so we purchased tix on AA to CZM from Chicago for $394/pp and I saved the miles for Bonaire since those flights are more expensive (and surprisingly, we found better redemptions at 20k/pp). Every once in awhile, BON, RTB, and PLS can be had at 20k/pp or less on AA but I can't detect the pattern of when they're released. I also saw CZM award for less than 15k this year but the connections weren't ideal. AA awards have worked great for us for the Caribbean over the years.I often get great FF award travel on AA to Cozumel. I book 328 days in advance (330 days is the max and flight prices usually drop a few days after they open dates). Last year we snagged one way for 12k from Wichita the week after Thanksgiving.
Flexibility and advanced planning is key.