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With the case and protection you have I think it should be OK in your wife's pocketbook. Most of the Caribbean uses the same power as the U.S. so charging should not be a problem (check where you are going to be sure) I have never carried my Reader on a trip, I just got it a week ago, but have always carried much camera equipment and never had a problem with airport security either here or the Caribbean. The X-ray machines should not hurt the reader.
The best advice I can give you is HAVE A GREAT TRIP!! Dan
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