ESTA - Help!

I read the transit thing the same way as you did (i.e. you're just in the US to go somewhere else). As you're hanging around for a while i'd say it's not transit. Why would they care where you're going after your holiday there? None of their business (they probably disagree with that ?)

That employer question is just really badly put isn't it? Why they can't be clearer about what they mean is beyond me. Has he had a previous employer? Maybe you could tick yes because he has in the past worked for someone else?

Hi,

it's $14 if you apply directly rather than using a travel agent. There's lots of fake websites or agencies that charge a fee to do it for you. Are you using this website? https://esta.cbp.dhs.gov/esta/

We travelled earlier this year but I don't remember the employment question. Might have changed since then i guess.

As for the transit question, i'd say No. We were in a similar position - we travelled to NY for 5 nights then on to Aruba. We didnt have any problems by clicking no anyway! I see transit as more of a layover type thing, a few hours stuck in the airport waiting for a connecting flight.

I would also read transit as a stopover on a flight or for a cruise you only need to have an address for the first night in the US. Don't remember the employment question either but basically think they are just checking if you are employed which he is so answer yes.