I am travelling to Thailand this month in the shoulder season. I will be going to Chiang Mai, Koh Phi Phi and Koh Lanta.
I intentionally planned a loose itinerary and only booked my first few nights accommodation in Chiang Mai after I land. I had the idea of walking around finding suitable hotels when I reached my destination, not booking ahead (I know it's a different place but I visited Bali last year and found this approach was easier and cheaper).
Would this approach be ok? Or would it be difficult?