From J1 TO ESTA the same year
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With these and similar issues, the question is always: Does it look like you'll enter the US with an intent to stay?
In theory, you should be able to re-enter the US as a tourist and be allowed to stay a full 90 days. In practice, they may look at you funny and make some comment about your visa. For that case, it is very important that you tell them that you're entering the country under ESTA, not your J1, and that you bring a printout of your ticket to Montreal with you to demonstrate that all you're back for is to finish packing up so that you can leave for your new place (because you can't take all your stuff with you on the cruise; ideally, the Montreal flight is only a few days after your arrival). If the place where you were studying has a decent international office, you can, in addition, ask them to write a letter confirming that you have finished your classes, and that you only return to the US in order to leave again.
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Source: stackoverflow.com
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