Tokyo and Osaka are both great cities with lots to do but in terms of things to see Tokyo holds a lot more. Osaka is (imo) more chilled out and funky. A great place to meet some locals and soak up the athmosphere. I don't know either city too well as i only had 5 nights in Osaka and 1.5 weeks in Tokyo, but here is my view:
Tokyo:
Best view of the city can be found on the sky deck of Mori Tower in Roppongi. Costs 1,500 Yen to get to the observatino deck and another 300 Yen for the sky deck. You can grab food and cocktails at the top and enjoy the fantastic view over dinner. Amazing. Just avoid going on a rainy/cloudy day :p
In Shubuya you have the famous Hachiko crossing. There are a few places to enjoy the view of hordes of people crossing the road. One of the cheapest is probably to grab a coffee in the starbucks there and you can get a good view and take some photos/video. It's quite a sight!
Daibo holds some nice museums with tokyo disneyland also nearby.
At night be sure to check out Shinjuku. It's a pretty crazy place and supposedly where a lot of Yakuza hang out. One of the red light districts can be found around Shinjuku.
Akihabara is the place to go if you like manga/anime and you can also find some good but cheap electronics there. I saw a few things i hadn't seen beefore in Akihabara.
Asakusa is a good place for picking up souveniers. Also a lot of temples and cultural things and you can also find the river ferry port here and take a trip up the river. I would recommend a wander around Hama Rikyu gardens entry for which oyu can get inclusive with a ferry ticket form the port.
Osaka:
In addition to the 2 recommendations above i would add the Osaka aquarium Kaiyukan. It's one of the largest and most impressive in the world with a central tank holding 2 whalesharks and a manta ray. If you like a good spa then take a look at Spaworld. I think it's 1,000 Yen for the day with an extra 1,000 Yen for the water slides at the top.
Like Tokyo it's well worth taking in some of the nightlife, even if you're just wandering the streets. America village and Europe village are impressive with doton-bori housing some great places for food and drinks and some enourmous and colourful video screens in the street.
I could go on for hours about these cities but i think i covered my favourite things :p and i don't want to spam the boards! Enjoy Japan. It's a fantastic country with some great people. Be prepared to struggle if you are expecting people to speak English. I was surprised at how few did but they are now teaching English at elementary level so younger people will be better at English.
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