Hoping for the best is not an option with the USA. Sure, some get away with roaming around north america but some come a major cropper. Hasta Alaska (I think it was) was a case in point. Spent years getting from Ushuaia to North America, got through maniland USA and then Canada and then was refused entry to Alaska, so that was the end of a several-year-long dream. He did eventually go back home and establish a normal life and then did return to pick up his dog and his Kombi and finish the journey.
Extreme case but the rules are clearly stated and especially nowadays there isn't a lot of good will at any border and especially not at US borders. If you plan on spending more than 6 months in North America before heading into mexico and then further south, then I suggest allowing for the fact that you might have to fly out to a non-contiguous country to reset the clock.

US Government does have a very responsive email contact so you might want to run your plans and intinerary past them (use a friends email address perhaps) to see what the official position uis



from https://help.cbp.gov/app/answers/det...-b1-or-b2-visa

However, there seems to be a bit of an escape clause that if you go in to Canada for considerably longer than the 30 days quoted, they are likely to regard your return as a new visit. Possibly - but of course the officer at the gate can tell you to get lost just because of the colour of your sneakers and there is little you can do about it.

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Tony
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