Can I enter Thailand on a 60-day tourist visa and later apply for a retirement extension?

Good luck 🍀

Or you can fly out and come back on a new tourist visa

Actually NO you cannot 😮

You can't go directly from a 60 day tourist visa entry stamp to a year extension based on retirement 😕

You need to first apply for an in country 90 day Non-O visa, THEN when that 90 days runs down and you have your funds seasoned the requisite 2 months in a thai bank account in your name only you can apply for the year extension.

In order to apply for the 90 day Non-O visa you need to have between 15 and 21 days left on your current stamp (to cover the under consideration time period)

The process works like this

Enter get 60 days

1 - go to the immigration office and apply for an in country 90 day Non-O visa (there is no seasoning of the funds at this stage, you only prove that the funds came into your thai bank account from abroad) pay 2000baht

2 - Wait the under consideration period (Most offices are 14 days, Chiang Mai is 20 days)

3 - Go back and get the Non-O visa and a new 90 day stamp inked in (free)

4 - when you have 30 days or less left on your new 90 day stamp and your funds have been seasoned the 2 months in your account go back to the immigration office and apply for a year extension for 1900baht. They are issued on the spot.

I have a few friends on retirement visas. So I am not talking from person experience,... but from what I understand.

There are a couple of ways to do the retirement visas each with different benefits and requirements. I *think* one of the big issues is insurance requirements. I would get information on both options and make an informed decision.

Yes you can