2 week first solo trip itinerary (August/September)

Nothing to be scared about. Easy country to visit. I'd choose less destinations though. If you like beaches skip CM. If you like mountains skip the islands.

Everytime you move you lose half a day or a full day.

It is a nice first trip. What are scared of? Easy to meet and chat with others excursions can be a good way, personally I would stick to the one island. And if you are not diving then just do Samui.

Hey all, with @krabi144956186's comment it makes me think I should do one less day in CM and add a day to either Koh Samui or Koh Tao (idk if I should replace either for Koh Phangan). I also wouldn't to stick to one island for 4/5 days and miss out on the other. With 2 days that lets me get to see both was my thinking!

Let me know!

Aug 31: Bangkok arrive at 10:50 AM
September 1: Bangkok
Sept 2: Bangkok -> Chiang Mai (Flight/Train)
Sept 3: Chiang Mai
Sept 4: Chiang Mai
Sept 5: Chiang Mai -> Surat Thani (Flight) -> Koh Samui (Ferry)
Sept 6: Koh Samui
Sept 7: Koh Samui
Sept 8: Koh Samui -> Koh Tao (early so i get my day in Koh Tao)
Sept 9: Koh Tao
Sept 10: Koh Tao -> Bangkok (Bus+Ferry)
Sept 11: Bangkok
Sept 12: Bangkok
Sept 13: Bangkok flying out 3:30

If not diving go to Koh Pha Ngan. It's more your age group.

Book your flights, international and domestic. Then just play the in between by ear. You don't have to decide on which island yet. Don't need to until you arrive at ST airport and need to book bus and ferry yo an island.

Looks good to me, I'd probably fly from Bangkok to Chiang Mai, it's often cheaper or as cheap as trains/buses anyway and takes a lot less time! Understandable to be nervous for your first solo trip but Thailand is a good country for it, the people are friendly, most of them speak English and you'll find other travellers everywhere.

Most Thais barely speak English. It's only in tourist areas they speak it.

Yes, I meant more for the places he's going :)

So Krabi you would suggest this?

Aug 31: Bangkok arrive at 10:50 AM
September 1: Bangkok
Sept 2: Bangkok -> Chiang Mai (Flight).
Sept 3: Chiang Mai
Sept 4: Chiang Mai
Sept 5: Chiang Mai -> Surat Thani/Samui (Flight)/ -> Koh Tao (Ferry)
Sept 6: Koh Tao
Sept 7: Koh Tao
Sept 8: Koh Tao -> (early so i get my day in Koh Tao)
Sept 9: Koh Tao
Sept 10: Koh Tao -> Bangkok (Bus+Ferry) or flight
Sept 11: Bangkok
Sept 12: Bangkok
Sept 13: Bangkok flying out 3:30

but to replace Koh Tao for Ko Pha Ngan??