I am a US citizen staying in Pattaya. I was admitted Nov 9, no tourist visa, and just extended to Jan 22. I'd like to go to Ko Lipe on the 21st, via Langkawi Island Malaysia (air), and return the same way. Will this give me another 45 day visa exempt stay in Thailand? Will it raise any eyebrows (too many consecutive trips to Thailand)?

You provide too little information about your previous immigration history in Thailand to give you a considered answer. If your arrival on Nov 9 was your first ever visit to Thailand, there ought to be no trouble at all returning for a further visa exemption after a few days in Langkawi and Ko Lipe. However, if you are a frequent visitor, the wrong official might decide you spend too much time in Thailand as a tourist. Arriving by land would then be safer.

12 hours ago, BritTim said:

if you are a frequent visitor, the wrong official might decide you spend too much time in Thailand as a tourist. Arriving by land would then be safer.

I've been to Thailand many times; once per year, 3 months per visit, for about 16 consecutive years before the pandemic. But Nov 9 was the first time I've been admitted here in about 3 years. Why would arriving by land be safer?

Edited December 22, 20223 yr by leosmith

33 minutes ago, leosmith said:

I've been to Thailand many times; once per year, 3 months per visit, for about 16 consecutive years before the pandemic. But Nov 9 was the first time I've been admitted here in about 3 years. Why would arriving by land be safer?

With your history, you'll have no problems flying in.

42 minutes ago, leosmith said:

But Nov 9 was the first time I've been admitted here in about 3 years. Why would arriving by land be safer?

Your history no problem flying in visa exempt. 

 

Be aware that the airline will most likely require onward flight.

 

Regarding entry via land borders visa exempt there is a cap of 2 per calendar year and you won't have any issues even with more recent history staying in Thailand.

 

Stick with your flight options.

 

Koh Lepi ....assume you have been there. I wouldn't go with a free ticket. 

 

Edited December 22, 20223 yr by DrJack54

11 minutes ago, DrJack54 said:

Koh Lepi ....assume you have been there. I wouldn't go with a free ticket. 

Koh Lipe, not Lepi - typo or a different place? It was a snorkeling paradise in Jan of 2020 - has it changed? Not much else to do there, so I guess I see your point if you don't like that.

5 minutes ago, leosmith said:

Koh Lipe, not Lepi - typo or a different place? It was a snorkeling paradise in Jan of 2020 - has it changed? Not much else to do there, so I guess I see your point if you don't like that.

Yep typo.

If you have hobby that you enjoy there go for it.