Overstay it’s not recommended if you plan to go back to Thailand later. You’re entitled to a 30 days visa exemption or free stamp upon arrival. This can easily be extended with additional 30 days at your local immigration at 1900 baht. 30 days overstay could potentially give consequences beyond a
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baht fee at the airport. An agent will extend your extension without any issues for you for 4000 baht including fee and everything.
I agree with Chris. Two tourist visa should be possible if you don’t have any recent history travelling in and out of Thailand, but instead of travelling back to back on two tourist visas, I personally would prefer a tourist visa with multiple entries. Then you’ll cover your whole stay in one simple visa. It might be a bit more expensive than two single entries visa, but anyway. And you don’t need to use time to apply for a second visa in KL. These are the general requirements at the Thai Embassy in Ottawa.
. If you fulfil the requirements you can apply directly for a 90 days Non O visa. Then you’ll don’t need to concern about your return. The requirements are quite straightforward, and then you don’t need to do any extension on your tourist visa at the immigration in Thailand either. This is from the Thai consulate in New York.
There’s no official limit on visa exemption by air, but people get pulled aside and questioned quite fast now. They are cracking down on longer stays and people travelling in and out of Thailand without visa or tourist visa. Several feedback over a longer period of time confirms this. This is another example. On their third entry by air they were told to get a visa next time.
You can as explained only extend your visa exemption one time and get additional 30 days on your visa exemption. The only visa you can apply for in Thailand is a Non O visa. So if you want to stay for 60 more days in Thailand after your exemption runs out, you don’t have any other options then get another 30 days visa exemption.