Corrected entry: Kevin's family is going on a trip to sunny Florida. Yet, Kevin's bag is packed with winter clothes.
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Correction: We do not know this. Kevin's bag is never opened by his family (that we could see anyway), and the bag he had with him in New York was his father's. This proves the above plot hole to be correct, as well: any clothes he wore he had to have bought while in New York.
redbaron2000