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3+ weeks in Thailand, Laos, Vietnam, and Cambodia on a tight budget

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My boyfriend and I are travelling to SE Asia for three weeks and a few days in July. We have never been to the area, and are not highly adventurous travelers. We are extremely interested in meeting people, seeing the area, hitting important sights, and experiencing the different cultures. We have a very tight budget, and don't want to spend more than $250 total on travel once we are there (*is that even possible? How much will we spend on food and accommodations?)

We are flying in and out of Bangkok and need advice on itinerary! We originally thought we'd go straight to Luang Prabang, then from there to Hanoi, down to Da Nang, then to Saigon, and from there to Angkor Wat/Siemp Riep. From there we were planning to head to a few islands on the way back to Bangkok to fly out. Obviously, this is extremely ambitious, and will cost a fortune if we are going to fly from place to place for the most part (we've been advised- please post your opinions- that trains down Vietnam are not the best idea, and same for getting to Laos from Bangkok...etc.).

That said, please post your thoughts on the best/cheapest/easiest places vs. those that can't be missed in this kind of short, intense 3 week trip. Also interested in all cheap flight finding suggestions. We are completely willing to take trains and buses if they're safe and somewhat reliable, but are starting to think that 13 hour train journeys are not the way we'll rely on to get around for the most part. Willing to compromise certain destinations for a better experience in fewer.

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