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My family lived in Japan for several years. We did not live within Tokyo itself, but more in the suburbs. Shinjuku is in the heart of downtown Tokyo. It is a shopping and transportation hub (we would catch the bullet train there). It will be expensive and crowded, but being the heart of downtown Tokyo, there will be plenty to do and see. Should be fun for a young, single person.
Based on our experience, you will find tourist help spots at the major train stations (and airports) where they always have some one that speaks excellent English. In the major department stores, it is hit and miss whether or not they have a sales person that speaks fluent English, but they will try. The same goes for restaurants. Best to learn a few phrases (and if you are not embarrassed, you can have a Japanese friend write out basic phrases on note cards for your use, like your home address in case you get lost you can hand it to a cab driver. This worked for us when we lived several years in South Korea).
One note. Younger Japanese are more likely to speak and practice English, but never assume any Japanese does not understand English until you know for sure. Some like to pretend they do not understand English when in fact they spent years in the U.S. as undergraduate/graduate students.
As my daughter has been planning this adventure for the last year she smartly chose to take Japenese language classes twice a week for the last year, now that she is there she says she can understand the written text with no problem very well and her speaking skills are adequate.
I went there last year. Shinjuku is a major business district of Tokyo, somehow like Time Square of NYC but much cleaner.
Young professionals all speak English to some extent. Older ones have more difficulties.
Since I can read Chinese characters, often times I could figure out what is going on without speaking. I imagine westerners will have more problems if traveling alone.
My daughter is now living in Shijuku for the next year, any one been there? whats it like?
Shinjuku is highly populated, extremely safe, very interesting, and a fest for the sights and sounds of Japan. Many young people walk around, fashionably dressed, and everything caters to them - i.e. food-snack bars, shops, everything.
Definitely go to YouTube, and do a search for 'Shinjuku' with the words 'streets' or 'walking' or something, so you can get a sense of what it is like visually. It's great!
She called me up this morning to chat, she said she hasnt spoken English in a week, shes fitting in nicely. I asked her if theres anything she misses in Montreal,she said i cant find Lays Sour Cream and Onion chips.
It's great and safe, speaking from the point of view of a past tourist.
Advice: tell your daughter to avoid Roppongi, it's known as a place with Nigerian scammers, yakuza and porn...you get the idea but good news: roppongi and shinjuku-ku are far away (10-15 kms) plus even Roppongi is safe at night. It's japan after all not africa.
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