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Thailand Trip: anyone been, any suggestions?

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Planning a two week trip to Thailand at the end of April this year and was looking for some suggestions; things you have to see, places you have to go, food you have to eat, ladyboys you have to avoid... I originally didn't want to, as it's an expensive trip and I feel guilty with all the med school loans that I have, but I've also been told by all my attendings that in twenty years I would regret not doing more things with friends and family during residency as opposed to saving an extra couple grand. And, from people who have gone, I have heard mostly that once you get there, everything is pretty cheap as hell. For those of you who have gone or done similar trips, did you use any companies to help plan the trip, did you just backpack and go to hostels?  A buddy of mine recently turned me onto googleflights and then roompro.net to book flights and rooms, respectively. Not sure of anyone's experiences. 

Looking at the room, it seems as though you can get rooms for damned near half off if you plan half a year in advance, seems pretty worthwhile, just curious as to everyone's or anyone's experience. 

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