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Help with Itinerary - Thailand/Malaysia/Singapore?

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I've been looking into booking a trip to some different places in Asia. My boyfriend and I just moved to New Zealand and figured we had a better chance of hitting up some of these places from this side of the world. That being said, I've been looking at trips to Thailand, Malaysia, or Singapore and only today realized how accessible each is to the other.

Would it be suggested to split these destinations up into seperate trips or, being there already is it suggested to do all in the same trip? Also, if we were to do this, how much time do you think we would need? Would we be better to have it all planned out prior to leaving, or sort of make it up as we go if we just know major cities we would like to see?

Lastly, I have also heard really great things about Bali too. In my mind this is a seperate trip, thoughts on this? Any advice would be so great as I've never been!

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