ESTA- Brain melt.

Thank you Marka55, a travel agent told us similar and this was my interpretation of the VWP. It would not be an issue for us to save the USA trips until January when potentially we may have to leave Canada anyway if tourists.

I have spoke with a very rude receptionist at the American Embassy in London and have emailed them regarding a tourist visa. I await response.

I am also conversing with customs in America through an email thread but they are very reluctant to advise me in layman's terms and keep throwing the same jargon I can see on websites. For example -

Read our first part of response. You are OK to visit U.S. under the Visa Waiver Program if you travel to U.S. from Peru. However, our law says that you must travel **with a valid round-trip ticket and your trip cannot terminate in a third country. You will encounter problem if you visited U.S. first for 80 days (for example) then went to Canada, Mexico, or adjacent islands for another 20 days because your total time will be over 90 days limit. However, Peru is not considered one of the adjacent islands so you are good to go:****

This may seem like a silly question, but how does the ESTA stop?! Is it when we fly out of America to a non bordering country? What happens if we get jobs legally in Canada / are allowed to go back as tourists and want to fly to America a couple of times to city break in a 90 day period, does it keep running over the 90 days because we are going back to Canada?

The ESTA does not stop, an ESTA only indicates that you are not the sort of person who would blow up the aircraft before it lands, you do not even need an ESTA for land entry to the US. The VWP entry to the US is different if you do it by air or land and if you are in Vancouver you may well find that crossing the border by land and then taking a US domestic flight from Seattle is a lot cheaper than an international flight from Vancouver, also VWP entries by land do not require the roundtrip or onward ticket out of North America that entries by air do. If you cross by land you have to pay US$6 and get a green I-94W form stapled in your passport along with the 90 day VWP entry stamp, if you fly, you may be surprised that you go through US entry procedures at the Canadian airport, not the US destination and you just get the 90 day VWP entry stamp. When you reenter the US within the 90 days, whether by land or air just point out to them the initial VWP entry stamp, but expect much the same interrogation as the first time. If your initial US entry was by land, then when you are leaving the US for the last time within the 90 days surrender the green I-94W form stapled in your passport, either to a Canadian border official if leaving by land or to the airline right at the boarding gate. If you are coming and going by land then do not surrender the green I-94W form stapled in your passport every time unless you want to pay US$6 every time, it is good for the whole 90 days so keep it until the final trip. Do not expect much useful information from the US government. A Canadian WHV allows you to come and go during the year as you please.

This may seem like a silly question, but how does the ESTA stop?!

ESTA approval does not stop just because you leave the country. It stops when one of these things happen:

1. The two-year approval period ends or your passport expires, whichever comes first Or
2. The US revokes it. This could happen because you do something that means you can no longer use the Visa Waiver Program (such as overstay) or because the US discovers you have taken up a life of crime or become a terrorist.

Your question is really about admission under the Visa Waiver Program, not about ESTA.

When you show up at a US immigration desk, you apply for admission to the US. Admission is always at the discretion of the immigration official. Having ESTA pre-approval or even a full visa does not guarantee admission. People applying for admission under the VWP are rarely denied entry, but it happens. The few reports I've seen were people who didn't realize that working in exchange for room and board requires a work visa, and someone who arrived at a land border & was denied entry because she had no access to funds.

Anyway, you arrive and apply for admission under the VWP. All goes well and the official either grants you a 90-day stay or a stay until your passport expires, whichever comes first.

The US has no exit controls. If you fly out of the US to another country, the airline notifies US immigration that you have left. (Same thing with a ticket on a commercial boat). If you leave by land or by a private yacht or some such, there is no such notice. What happens is that, once the 90 days is up, a computer puts you on a list as having overstayed the 90-days you were allowed. There is a way to prove to the US that you did indeed leave north America within 90 days (for example, you took a bus to Toronto and then flew to the UK), but it is a pain.

If you try to come back to the US, the official is going to see that overstay on the computer and deny you entry. It sometimes happens that someone who has been in Canada or Mexico for many months after leaving the US, is allowed to re-enter under the WVP, but you can't count on it.

If you plan to stay in Canada to work and visit the US every so often, then you are going to need a full B2 visa. Here is how the US Embassy in Canberra words it (it applies to everyone, not just Australians)

Travelling to Canada for the Canadian Working Holiday Program (WHP)
Applicants travelling to Canada for the Canadian WHP may wish to apply for a tourist visa prior to travel, rather than use the VWP. Most flights to Canada [from Australia] transit the United States, and if you are planning to spend longer than 90 days in Canada the VWP may not be appropriate for such a transit.
Additionally, WHP participants may wish to visit the United States from time to time while living in Canada. This again may require a tourist visa, rather than the VWP. Most short terms visitors to the United States enter on the B1/B2 Business/Tourism visa.

#12 The big difference to the advice for Australians is that most flights between Canada and the UK do NOT transit the US, so the case for going to all the time and expense of a B2 visa is much less clear cut. Also the problems of the US not knowing that you have left are only if you arrive by air and leave by land, if you arrive by air and leave by air or arrive by land and leave by land (and surrender your I-94W) there is no problem.

Thanks to both of you for your advice. We have decided to go for the ESTA/VWP as the priority has always been to go to SXSW in Austin then spend the majority of our time in Canada, anything else in The States is a bonus really. If we go down the B2 route we could be declined and then declined from VWP (I have read some peoples' experiences). It could mean we don't go to America again after Austin so be it. There's always Europe!