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SEA itinerary confusion...plan for Vietnam, Cambodia, Thailand

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Hi all!

I am planning the longest trip I have gone on thus far in my backpacking career. I will plan to go to SEA in December-January, ending up with a week or maybe now slightly longer in New Zealand on the way back. I have looked into a few itineraries and ideas and now am getting a little overwhelmed with possibilities.

The two constraints I have schedule-wise are that I need to be in Bangkok from Dec 30- Jan 6th for advanced massage course, and then 5 straight days at any time before that for the general massage course. I can do the general course in Chiang Mai or Bangkok so thought about doing a week in CM to explore a northern city.

So, this is: Dec 14- Dec 29 free (16 days), at least 5 of which would be in Chiang Mai prolly.

Originally I had this idea to get a cheap flight I found for under $100 to Hanoi, work down the coast using the trains, onto Cambodia, and then to accommodate schedule, potentially another cheap flight to Thailand or bus/train if schedule worked out.

But I also am wondering if at the end of a busy year (will have just taken pre-clinical tests for acupuncture school, might be pretty fried), if I should not miss out on the beaches in Thailand/Cambodia (Koh Chang or Sihanoukville look best fit for me if travel is not too much of a pain), maybe even Vietnam (where?) and do that for a couple days at first, or at some point. Laos looks awesome but maybe I leave this for another trip, just too much!

I also thought maybe I can go for a few days somewhere after I finish on the 6th- ie, a couple days in Cambodia then or beach or whatever.

Some things that looked very great are the following: Siem Reap, Preah Vihear, historical sites in Hanoi, Ha Long Bay, Hue, Hoi An, maybe the caves outside Dong Hoi, and of course stuff in Bangkok and Chiang Mai. A beach at some point sounds good as well as hot springs if possible!

I can't say I'm particularly convinced I need to go to Saigon, and Phnom Penh isn't crucial to me this time around.

In addition to all this nonsense, a friend of mine gigs at one of the fancy casinos in Macau and is begging me to stop by for a few days. Is Macau even worth it? It would be fun to hang but maybe I could drag him to meet up somewhere on my trip (though a free couple nights in a fancy hotel wouldn't be SO bad :) and I might even get a few gigs myself and make some decent money (I'm a musician also).

What makes sense here of maximizing travel time and experience and budget? My flights to/from Asia will be basically free, so I don't mind a couple cheap internal flights when it makes sense. I want to take train in Vietnam and Thailand when possible, buses are ok too if reasonable length (not interested in 24 hr ones this time).

Thank you sooo much in advance for helping a frazzled med student try to make a plan!

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