Been looking to book my vacaction for October but cannot decide where to go. Had initially decided up Japan, visited there a couple of years ago (Stayed at Conrad) and it was just THE best holiday ever. Loved everything about it, Hotel was exceptional, ANA flight the best (free upgrade) and the people were so politie. Stayed 8 days and it was the most relaxing holiday I've ever had as such had always planned to go back.
Was in the process of booking my trip to go back (Hilton Tokyo this time as Conrad price was high) but then a friend mentioned Hong Kong to me. And the more I thought about it, and the more I looked into it the more it appealed. Since I was going to be spending so much on a holiday, why not go somewhere new? The trip was going to be more expensive, iro £700 more for hotel/flight between two but I thought it'd be a new adventure.
However, in the back of my mind I still would like to go back to Japan.
I was wondering if anyone has been to both places? If so how do they compare? I just cannot make my mind up. It does seem daft to spend so much to go back to a place you have already been when there is so much to explore.
You can have a fun holiday at either. Bear in mind, however, that Hong Kong is a smallish place, although you can also spend a night or two in Macao. Other than that, as a US citizen, you need a China visa to go anywhere (with very limited exceptions, but few westerners go to places like Hainan island from HK). Chinese visas cost $150+ and take effort to get.
I personally am not sure there is 8 days in Hong Kong and Macao, but if you have 8 days in Japan, there are lots of places to go to other than Tokyo.
If staying on Hilton points is important, you could, for example, fly into KIX and stay at the Hilton in Osaka and commute (it's inexpensive and about 30 minutes) by train to Kyoto and Nara. Or you could go for the Hilton resort in Odawara, south of Tokyo.
I say go somewhere new! Hong Kong is fantastic. I think you could fill out 8 days if you include Macau, the New Territories and even a guided day trip into Shenzhen/Guangzhou. I did that a few years ago - IIRC it's easy to get a package tour visa to go in for the day - the tour company in HK handles it.
Or you could do say 4-5 days in HK and then hop over to Singapore or Bangkok or even Phuket for 2-3 days.
As a general rule, all else being equal, I would visit the city that's new to you. I lived in Tokyo during my high school years and return often - my family just returned from a trip there last week - so my bias is to say "Japan!" but, in your shoes, I would try Hong Kong.
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That was my concern - whilst out initial base was going to be Tokyo, we'd planned to travel to Osaka, Kyoto, etc as there was plenty we missed on our last trip. In addition we have actually budgeted 11 days, which makes Hong Kong even smaller.