Will I face issues entering Thailand for 53 days without a visa if I plan to travel outside the country first?

@Arthur *******

Sorry I didn't read all the replies. You may want to concern about the airlines allowing on the flight from NY. That's the larger concern - Thailand is all to happy to have infrequent tourist. You should be ok but ... the visa exempt is for 30 days.

Okay, IF you already have your round trip ticket to thailand with the arrival departure spaced out over 53 days you're FINE. You won't have a problem boarding the flight in the US because you have onward travel (even though it's not within 30 days they aren't going to say anything to you about it) AND you're not going to be asked anything entering thailand because the passport stamping people at passport control know you can get an extension of stay for 30 days IF you want to. AND when you exit the country to go to Cambodia you're not going to be asked anything when you stamp back into thailand on a new 30 day vsia exempt entry, and even if you were you have onward travel back to the US.

You won't have a problem with passport control stamping into the country.

I'd say it's easier to get a single entry tourist visa which would stamp you in for 60 days. That way you don't have to go to the immigration office for a 30 day extension for 1900baht like you would if you entered on a 30 day visa exempt stamp.