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I personally hate Roppongi, but most westerners like to go there to party because they can actually communicate a bit. I go there once in a while but I stay off of the streets and go straight into the club. Between the US military guys acting like drunk assholes, and the Africans acting like they're from NYC trying to lure you into their shitty, overpriced, wanna-be strip clubs...I'd say you're best bet is to skip the street. If you do happen to go to Roppongi...go to a club called Feria. It's right accross the street from a popular club called Velfarre (which blows). In Feria you'll find mainly Russian model chics...and tons of Japanese whores too. It's a must.
If you want the real deal Japanese culture thing then stay outa the big cities. Of course you have to check them out...but spend your time off the beaten path.
Yoyogi is alright, lots of Westerners.
Listen to ADG and get a book and plan out the trip. If not you'll be scatter-brained. Hakone is a must if you come in the winter. Hot springs and the mountains are awesome.
I used to live in a place called Urawa which is about 45 min. north of Tokyo. That's a cool little city and the people are much nicer than in Tokyo. Omiya is cool too which is a little north of Urawa - lots of mobsters and strip clubs there. Pretty dirty city.
Nishi-Kawaguchi has more massage parlors than you'll be able to visit. Most of them don't accept the round-eye...but you'll find some that do.
Oh, I almost forgot...you HAVE to check out the fish market Tsukiji. It's the biggest fish market in the world and it's simply oerwhelming. Check it out online and you'll see what I mean. It's closed on Sundays. Get there early like 6 or 7 AM. You can't see the Tuna auction anymore because they recently closed it to the public...but it's well worth it.
And...if you're looking to teach English and stay in Japan for free in exchange for 12 hours of teaching a week (usually broken into 2 or three days)...PM me and I'll point you in the right direction. No VISA needed. No pay, but free place to lay your head.
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