2. Any limit to how many times I can do that in a year?
Thanks
Answer summary
A Singaporean citizen can enter Thailand visa-exempt for 30 days, which can be extended once for an additional 30 days. For a longer stay, obtaining a 60-day tourist visa before arrival is advisable, which can then be extended for 30 days, totaling 90 days. After this, they would need to leave the country. There is a limit of two visa-exempt entries by land per calendar year, though there is no strict limit for air entries, subject to immigration officer discretion. Additionally, options such as applying for a NON-O visa exist for longer stays.
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If you want 150 days you can do what I just recently did. 60 day visa, 30 day extension, 2 land border runs. You can get another extension after your first visa run if your landlords cool enough to do another TM30 after your border run but my landlord is a slack ass so I did 2 border runs. Either way will be fine for 150 days
As a Singaporean you can buy a 60 day tourist visa from the Thai Consulate in Singapore. That will give you 60 days entry. Then you can extend that once for a further 30 days and therefore you will have 90 days straight. After that you must leave. I did the 60 day TV Last year and extended it myself in person at my local immigration office and it cost me 1900 baht and half a day to do it. Good luck. 👍
There is a limit of 2 exempt entries by a land border in a calendar year. Technically no limit via air, until the immigration officer decides you’ve been trying to stay too long without a correct visa.