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Two weeks isn't a lot of time when he will be having fun.
Myself, I would prefer to stay in the one place for a little longer, rather than wasting time at airports etc...
I would probably drop one of those destinations altogether myself... Hard one to call. I definitely recommend Phuket.
His schedule looks doable, but only just IMO. Maybe drop one of those nights in BKK? CM is worth seeing I hear too... I haven't been yet.
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