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Japan, Hong Kong, Singapore - advise is needed

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I've been to Tokyo, HK and Singapore 20 years ago on a business trip. I am planning a vacation now and would like to get some opinions. We are a couple in late 50s-early 60s, well travelled in Europe.

1. We are going to Japan for a week - from Apr 29 to May 6. We are meeting up with our friends, also tourists, there. I heard it's a golden week in Japan. Does it mean we will have a super hard time of getting hotels, train tickets. etc ? The plan is to spend 3 or 4 days in Tokyo and then 3 or 4 days in Kyoto. I know it's not nearly enough but we don't have much flexibility there.
2. Since we are flying that far we thought of going to Singapore. We are aware it's another 7 hours away from Tokyo but the same corner of the world. We've seen pictures in travel magazines and are very anxious to get there. we were thinking of spending 2-3 days there.
3. We also thought of spending 2 days in Hong Kong. I've heard different opinions on it - that it's the most western place of all and doesn't have the same authentic feel. It seems like a good stop for us. Though we can change it for another city.

So the itinerary would be
- fly from New York to HK, non-stop(?), stay there for 2 full days
- fly HK to Singapore, stay there for 3 days
- fly Singapore to Tokyo, 3-4 days in Tokyo, then Kyoto.

I am asking people who've been there and travelled that part of the glove - how does it sound?

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