Hello fellow travelers,

My partner and I have been backpacking for quite a few months now. Our home is in the UK, of which she is a citizen. We are headed to the USA in June.

As far as I have been able to research, with an ESTA she is required to have an onward/return ticket. This has never been an issue before because we have simply traveled to the US and back home. I know on a few occasions in other countries, an airline has asked for proof of onward travel before letting us board (we have never been asked at immigration itself). It sounds like we are going to need to book a ticket out of the US, within the 90-day period allowed under the ESTA.

Obviously we do plan to leave the US within the 90 days, but our plan is to travel on to Canada and spend some time there. Before booking a ticket to Canada (or elsewhere) out of the US I have a few questions:

1. Some things I have read indicate that a ticket to Canada will not work, as the ESTA traveler is expected to leave "North America" not just the US. We are not prepared to book onward travel from Canada as we don't know when or where we will be going from there. In that case, should we wait until the day of travel and book a refundable ticket out of N. America (e.g., back to the UK), so that we will be allowed to board?

2. Assuming we use this solution, in the event that US immigration asks us about it, we are going to have to say "We understood an onward ticket to be a requirement which is why we bought this. We do plan to return to the UK but we are going to Canada first." It seems strange to buy a ticket just to tick a box when our plans are otherwise, but is that what they want us to do?

3. Finally, assuming all this goes smoothly and we travel on to Canada from the US, is she forbidden to come back into the US at all until we have left N. America? I understand the rule is in place to prevent visa runs, but what if we were in Canada for several months and wanted to take a straightforward return flight in and out of the US for a week or so? Some things I've read seem to say this is not allowed, but is it still at the discretion of the immigration officer?

I have read quite a bit of conflicting information so would appreciate any help--especially if you can link or refer me to official sources.

I have been to: the Bahamas, Barbados, Cuba, Curacao, Dominica, DR, Grenada, Guadeloupe, Haiti, Jamaica, Martinique, PR, St. Lucia, T&T, and the USVI.

I was thinking about visiting some other islands this upcoming summer, but was wondering the best way of getting around without having a set itinerary. Some ideas for islands to visit are: Sint/Saint Martin/Maarten, St. Kitts & Nevis, Anguilla, Saba, Satia, and possibly St. Barts.

I don't like just hanging out on a beach. I much prefer, exploring the actual islands and/or scuba diving. So these are my questions: Is my best bet a r/t to one of the islands and then local flights/ferries? Do any or all of these islands expect an onward or return ticket off of their islands? What's the best and/or cheapest way of getting around (I wish there was an air pass)? Considering my interests, from your personal experiences (I can read the guides) how much time would you spend on each island if you do not want to just lounge around?

Thanks