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Travelling to Thailand from U.S. this June/July

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Hi there!

My friend and I are planning a 3 week trip to Thailand this mid-June-July.

I need some help/advice from those of you that are seasoned Thailand travelers:

-Approx. how much money do you think we'd each need for 3 weeks accommodation (mid-level)/food/fun (tours, spending money). I understand that it will be low season this time of year....

-Should I book all of our hotel stays and train tickets in advance? Or is this something I can do once we arrive?

-We are flying into Bangkok and plan to spend a couple nights there ---any MUST SEE activities? We definitely want to check out the river market, eat some good food, and hit up some fun bars (at least one night).

-After the first couple nights in bangkok, we are heading to Chiang Mai to work at an elephant camp. We plan to take the train there, but after a couple days there, we plan head down (yes, all the way down) to southern Thailand to one of the beach towns (likely koh samui, but would like your input/suggestions).
-Should we take the train or fly from Chiang Mai to Southern Thailand? I realize the train may be very slow and take a couple of days. Is it possible to get a cheap plan ticket?

Sorry, so many questions! I have been researching all of this to no end, but I'd prefer to get advice from people who have been there first hand.

Thanks!

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