ESTA reentry to USA after very brief initial stay in NYC. (2 weeks NYC, 2 months Canada, 2 months USA)
Upvote:-6
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.
Upvote: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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