Would it be a bad idea to not book hotels ahead in Thailand?
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As a fellow traveller and often backpacker, I would advise you to do so in most places, but I don't know how long are you staying in Thailand. Visas can go from 2 weeks to 3 months, so if you intend to stay only 2 weeks then I would recommend to plan ahead so that you won't lose any precious time searching for a place to sleep or even changing accommodations (if you stay somewhere on the run and you end up not liking the place).
My personal approach is to not plan ahead and book places as we travel, 1 or 2 days before and only for 1 or 2 nights (so that if I don't like the place, I can change it without loosing booking costs) and extend the stay for as much as I like.
Also, if you end up staying at hostels ( for the simple fact that you meet alot of travellers and can get good travel tips and booking & restaurants recommendations) you should know that many hostel brands give discounts if you book with them in the next destinations (if there is one). Good luck and safe travels!
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