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Thailand, Myanmar and Cambodia in June

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We are in the beginning stages of thinking about a trip to S.E. Asia in June, 2016. We have to go in the summer as my husband is a teacher so the earliest we could leave would be around June 7th. If I'm reading prices right and we could keep hotel costs to around $100-$150 night average we could probably swing up to 3 weeks.

Our interests are history/nature/food and culture - we care less about nightlife and adventure (in our fifties so long treks or rock climbing are not for us, but would enjoy snorkeling or easy kayaking, several hour hikes).

Initial itinerarythought:
4 nights Bangkok
3 nights beach resort

Question One: I gather the Western gulf is the best that time of year - or is a beach town wasted in June?
3 nights Chiang Mai
3 nights Siem Riep
1 week in Myanmar - maybe including a river cruise

Question Two - while on the map Chiang Mai and Siem Riep look close to each other I gather the only way to get from one to the other would be to fly back to Bangkok - can this be done in a day (getting from one to the other)?

Question three: how safe/easy to use is air travel in that region?

All advice and insights would be most welcome. Thank you in advance.

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