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Questions on first backpacking trip to Southeast Asia

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On the first week of December I'm going to go on a backpacking trip to Southeast Asia for my first time and I'm thinking about going for about 3-4 months until about March.

As a preliminary idea, here's my thoughts...

Fly to Melbourne, Australia for a few days, then Perth / west coast (Coral Bay, Ningaloo Reef, etc) for about a week. Then from Perth, fly to Bali and work my way north with no set plan or itinerary. Seeing many places along the way.....Indonesia, Malaysia, Philippines, Singapore,Thailand, Vietnam, and Cambodia.

My questions are....
#1 Should I do it the other way around? Start perhaps in Hanoi and work my way south to Indonesia then finish in Australia? I'm sort of leaning this way as I'd like to be in Western Australia in March to swim with whale sharks. Then perhaps flying to Central America directly from Sydney, but that's another topic.

#2 Since I will be there for both Christmas and New Years, how is it in Southeast Asia for the holiday's, and is there anywhere in particular that's amazing to be for them?

If you have any must see places or things to do in each of the countries listed above, I'd appreciate hearing about them! If it helps, I'm not scared of traveling anywhere, no matter how dangerous it may be. I'm in my mid 20's male, tall, and travel smart, I've been in some seedy areas before and ended up just fine.

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