I’ve literally just came back from New York as a lone traveller. As long as you have you an ESTA, you should be fine. I wasn’t asked for any details on accommodation etc.
There shouldn’t be a problem unless you have other issues. Your not likely to be asked anything more then
There may be other questions but they will be very simple like that. Just remember to only answer what your asked. Don’t give while stories and keep it as short as you can.
What your purpose for visiting? – Site seeing.
How long will you stay? – Two weeks.
That’s probably it. They might ask:
Where do you plan to stay? – Hotels along the route.
Being in my lower twenties, I’ve never been grilled either at JFK, ORD or LAX (the latter of which was after the VWP extra security measures were implemented), and I was travelling alone for plain tourism.
What I’ve been asked is:
That’s it, never been asked anything besides that, not even where I’ll be staying (which is stated in the ESTA), and above all, I’ve never been asked to show any documents besides my passport and customs form (first visit) or APC receipt (subsequent visits). Not that I had anything else with me either (I rarely bring booking confirmation printouts with me).
I recommend you use an APC kiosk at JFK (I assume you’re entering the US there?), because anecdotal evidence suggests you’ll get asked fewer questions (although that wasn’t the case for me at ORD or LAX).
Furthermore, if you truly feel uncomfortable, you can always call the CBP at JFK and ask (1-718-487-5164 or 1-718-553-1643). Be 100% honest and detailed about the situation.
I’ve been many times as a solo traveller. I’ve been asked:
where I was staying my first night (guy in front of my wrote down the hotel from Pretty Woman!). It’s on the form when you enter.
what I was doing in the previous country (especially when I’d come on my own from Colombia(!))
when I was leaving (they sometimes want proof of an exit ticket. A bus ticket to Mexico or Canada is sufficient).
I’ve never been asked why I was travelling solo, and aside from the first night’s accommodation (which they actually looked up once to see if it was real), they’ve never asked further than this.
Travelling solo is more common than people think. It’s what many months of my travel has been. Enjoy it!
Unless you have any other adverse immigration issues outstanding that you haven’t mentioned, you are unlikely to have any problems at the border.
I visited the US in 2016 in fairly similar circumstances as you, lone traveller, first nights hotel booked, return flight 3 weeks later. I was asked the purpose of my visit and upon giving it (attending conference and then travelling) I was then asked if I had any documentation related to my visit, I said no (I hadn’t anything printed out, just emails I probably couldn’t access there) and immediately thought this was going to be a problem.
The immigration official just stamped my passport anyway and let me through, the entire process was 2 or 3 minutes at the booth.
Remember, you have gone through a layer of vetting already by getting the ESTA, and while it isn’t a visa, you can bet it’s considered in the visa grant process at some point.
No. Nobody cares about you moving around to different – yet undefined – hotels, or about arriving alone – many travellers arrive alone, and travel around.
The questions will focus on ‘are you going to leave as promised within the period of your visa-free stay?’ – meaning they might inquire about your situation at home – do you have family, a house, a job, a return flight, etc. They try to find out what the chances are that you plan to stay in the country illegally, and if they think so, they will deny you entry. If you are convincing that you plan to fly back home, you will have no issues.
P.S. if you mention that you’ll meet with your girl friend, make sure to mention that she is not from the US, but will fly back with you to your home country. Having a US girl friend can look like you might just stay with her forever.
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