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I have booked a flight to NYC in February, where I am due to spend 2 weeks. After this, I intend to get the bus from NYC to Toronto and from there spend 2 months travelling in Canada, before returning to the USA for 2 months to travel down the West Coast.

When I booked my flights, I was unaware of the ESTA complications. I'm now aware it would have been wiser to start in Canada, not New York, but unfortunately, I cannot change my tickets.

  • Would the 90-day 'clock' start ticking as soon as I enter New York and continue to do so even in Canada? Or could the ESTA be frozen or even reset, seeing as I'm only spending two weeks in USA and 2 months in Canada?

  • Would it be more sensible to fly from NYC to Toronto (so it's clearer I'll be out of the USA after 2 weeks?

3

The ESTA is an authorization to fly, or sail, into the US. It is not the framework that regulates your entry and stay in the US. That is the Visa Waiver Program. An ESTA is valid for two years, usually, or as long as your passport is valid, if the validity is shorter than two years. People driving/walking into the US don't need an ESTA.

There is no such thing as an "ESTA complication". It's the VWP 90-day rule that prevents people from doing visa runs that seems to be the complication... As mentioned in the comments, Does the 90 days VWP rule expire if you travel from the US to Canada? answers your question. Going to Canada, which isn't your place of residence, will not reset the VWP clock, whether your drive or fly. Your overall stay USA+Canada+USA will be on one 90-day visa waiver.

As you said yourself, you should start with Canada, then go to the US. As it is now, your planning will make you overstay. You should either change the plans, or apply for a B2 visa.

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    Explain the downvote. – user67108 Dec 13 '17 at 7:04
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When you would exit the USA it would mark you exited from the country. Once you come back into the USA you might have to reapply for ESTA (usually 72 hours before). So I think it should not be a problem in your case. Because ESTA allows multiple entries, it just does not allow the stay of over 90 days.

https://help.cbp.gov/app/answers/detail/a_id/1126/kw/esta/session/L3RpbWUvMTUxMzEyODE4NS9zaWQvNVluXzEzQW4%3D

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    Hi and welcome. I'm afraid this is incorrect. You don't need to reapply for ESTA (it lasts two years), but there is a problem with the 90-day rule, as the trip to Canada doesn't reset the clock (see under "If I am transiting through the United States to Mexico, Canada, Bermuda or the islands in the Caribbean under the Visa Waiver Program"). – Zach Lipton Dec 13 '17 at 1:37
  • Thanks for the clarification. Sorry about the information I misinterpreted. – Anon_Singh Dec 13 '17 at 3:54
  • No worries. Welcome to the site, and I hope you contribute many more answers. – Zach Lipton Dec 13 '17 at 5:29

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