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Japan or Thailand, or Somewhere New?

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This might one of those posts that can't be answered; or, perhaps the answer is: "only you know what you like to do and to see". In any event, here goes....

I am having second thoughts about an upcoming trip, particularly about the Japan portion.

I am currently booked for a trip in early October to Osaka and Kyoto for 6 days, then to Hong Kong for 6 days, then to Hawaii to visit a friend. My specific quandary is that I am considering substituting Bangkok, with a possible couple of nights in Chiang Mai, for Osaka/ Kyoto. My general quandary is: Do I want to return to places I have been before, or go somewhere new? I have been to Hong Kong several times, and I have also been to Kyoto once, and loved it; I spent four days, and saw just about every major "sight" there (even though I am not big on typical tourist sights usually).

Kyoto was fantastic, but do I really want to go back, or go back just two years after I was there last? I have not been to Osaka, where I plan on spending two nights; I am into food and exploring cities; but I am not really sure that I am that excited about Osaka either. I was originally going to do a few days in Tokyo (where I have been before), a few days in Kyoto, and maybe one night in Osaka; but I am traveling during a huge holiday weekend, which is followed by major conference in Tokyo, during which all of the hotels I am considering (I am one of those people for whom hotels matter; to me, where I stay an important part of my trip) are sold out. Additionally, the inflated expense of the hotels in Osaka (due to the holiday), and the prospect of crowded or full trains (which are not my favorite transportation to start with; as my general intelligence in many areas seems to be completely absent when it comes to taking trains), and full restaurants and sights etc. are concerning me. Additionally, one thing I was significantly excited about was going to Himeji Castle for the day; I just found out it is closed for renovations....And the combination of the high expense of everything combined with what I anticipate might be a particularly high "hassle" factor due to the three day holiday, for someone who prefers taxis and walking over trains is giving me pause. I am scratching my head wondering why I am taking this trip.

So I was thinking about returning to Bangkok, where I have been a few times (but have not been in eight years or so), but do not feel that I have "seen or done everything", and maybe flying to Chiang Mai, where I have never been, for a couple of nights. The idea of returning to one of those great BKK hotels, and enjoying the great food and fascinating nightlife, etc. Maybe this a better choice for me than Japan this trip(?).

If I did choose the Thailand option, any suggestions on how to split up 6 days, and what a good amount of time is in Chiang Mai; I was thinking two or three nights. Or feel free to suggest something completely different.

Thank you.

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