I saw quite a few people using their cellphones on an eastern Caribbean cruise, when we were in St. Thomas and San Juan (both American territory ports), but also overheard comments from several people that their phones did not work as promised. I'd say it's hit or miss. Can your little guy do email? Though it's pricey, you could send him a short email each day to say hi from mommy, and can do that from the ship.
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