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Will I be allowed back into the US if I go from Canada to Chicago (26 September), back to Canada and then Canada to Cuba (29 October to 5 November) back to Canada and then Canada to New York (28th December to January 2nd)? Does Cuba reset the 90 day count?

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    What is your nationality, and are you resident in Canada?
    – lambshaanxy
    Sep 19, 2016 at 4:54
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    OP can be a resident but not a citizen of Canada - we do not need ESTA. This makes no sense but apparently residing long enough in Canada and passing a ridiculously easy test leaches out the Bad(TM) the USA wanted to keep our with the ESTA.
    – user4188
    Sep 19, 2016 at 5:18
  • I'm voting to put this on hold until we know more about the OP's situation as per chx's comments.
    – hippietrail
    Sep 19, 2016 at 5:52

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Short and bitter: No, it will not, because Cuba is considered an Adjacent Island for Visa Waiver Program purposes.

However, if you're Canadian or resident in Canada, returning to your place of residence does reset the clock.

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  • Please don't link to questionable reliability third party sites only .gov especially travel.gov in this case travel.state.gov/content/visas/en/visit/…
    – user4188
    Sep 19, 2016 at 5:13
  • @chx I'm aware of that, but I'm also not aware of any place they bother to define "Adjacent Islands" on the official site. Last I checked, though, Cuba remained pretty firmly anchored off the coast of Florida.
    – lambshaanxy
    Sep 19, 2016 at 5:40
  • Usually governments go into nitpicky levels of detail defining such things as they are probably "legal terms" or somesuch.
    – hippietrail
    Sep 19, 2016 at 5:54
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    @hippietrail the adjacent islands are defined by statute.
    – phoog
    Sep 19, 2016 at 11:16
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In law, the islands are listed specifically:

The term “adjacent islands” includes Saint Pierre, Miquelon, Cuba, the Dominican Republic, Haiti, Bermuda, the Bahamas, Barbados, Jamaica, the Windward and Leeward Islands, Trinidad, Martinique, and other British, French, and Netherlands territory or possessions in or bordering on the Caribbean Sea.

You propose to spend 33 days in the US, return to Canada, travel to Cuba, and return again to the US 93 days after your first arrival.

It doesn't really matter; your first 90 day admission stamp would have expired anyway when you arrive in the US the second time. You won't qualify for automatic revalidation. So whether you travel to Cuba or not is irrelevant.

Here is your official reminder:

When traveling to the U.S. with the approved ESTA, you may only stay for up to 90 days at a time - and there should be a reasonable amount of time between visits so that the CBP Officer does not think you are trying to live here. There is no set requirement for how long you must wait between visits.

Occasional short visits are fine. The intention is to prevent "visa runs", not to catch out tourists who are a little uncertain about "the rules".

At the border the second time, you should expect some questioning about what you were doing in Canada and Cuba, and you should be able to explain confidently. Aside from that I see no real issues with the itinerary.

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Doesn't matter. Let me repost the image from https://travel.stackexchange.com/a/61835/4188 to show you a rule of thumb where you need to be out for 91 days after being in for 90: cbp rule of thumb

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  • He's not proposing to be in the US for 90 days. Not even close.
    – Michael Hampton
    Sep 19, 2016 at 6:21
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    From personal experience I know that this "rule of thumb" is not strongly enforced. 3 VWP re-entries in a row with between 4 days & 2 weeks out of the US bewteen each one, and each stay in the US between 85 & 90 days, resulted in no extra attention or trouble from US immigration.
    – brhans
    Sep 19, 2016 at 21:05

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