My daughter is in Puerto Rico, she wants to stay for 90 days and then travel to Costa Rica, and then return to Puerto Rico/the US, she was told at the airport that some countries don't count as having left, apparently Jamaica, Cuba, and other islands close by, can she go to Costa Rica and then return to the US ( and will probably fly home from the US, she has an Irish passport.

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    Costa Rica is not considered "adjacent territory" for the purpose of the visa waiver program, but depending on how long she plans to be there before returning to US territory, and how long she plans to stay after her return, she might still have some explaining to do at the border. What's her full itinerary? – phoog Feb 15 '17 at 14:51
  • Basically she's at the mercy of the immigration officer at entry point. She could be allowed back in, and she could be denied. Basically it's a gamble. – Augustine of Hippo Feb 15 '17 at 15:38
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    What is your daughter doing in Puerto Rico? Is she involved with anything that would be disallowed under the VWP, like attending a university or working? If she is, doing visa runs and pretending to be a repeat tourist is a very bad idea. – Robert Columbia Feb 15 '17 at 20:22
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    @JonathanReez no, since it's part of the US, and I voted to close since the OP has not returned to add any info; I'd like to find a better dupe, one that is more specific to US/ESTA/VWP and visa runs. – Giorgio Mar 16 '17 at 13:24
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    My daughter is now coming home, she is on a gap year which is what a lot of young people do before starting university or after finishing university and liked Puerto Rico a lot and wanted to return , nothing more than that, she wasn't doing anything illegal, just spending time there, meeting nice people , she may go back jut to visit, not to do anything illegal or disallowed. – Shirley Mar 20 '17 at 0:25