I often get mail from people planning a trip to Tokyo, asking me to recommend some sightseeing spots. While there are many fun things to see around Japan’s capital, the reality is that the Kansai (Osaka) region is the better place to visit, with fabulous destinations like Kyoto and Nara and a thousand more years of history than the Kanto (Tokyo) area. If you are Tokyo-bound, though, here are some suggestions. Of course Akihabara is fun to visit, but if you want to really drink in the totality of otaku culture, try to be there on a Sunday after payday (which is the 25th of the month), when everyone is power-shopping and giddy with excess energy. If you like 8-bit gaming culture, hit a store called Super Potato, which has more classic console game stuff than you can shake a stick at. If you drink, make sure to go pub-crawling in Shinjuku’s east side near Kabuki-cho, or else head to Shinjuku’s West Side anv have some Suntory Hibiki in the bar from Lost in Translation. If you need to get across the bay to Odaiba for any reason, go out of your way to ride Himiko, the “water taxi” designed by Space Battleship Yamato creator Leiji Matsumoto. Another fun water-related experience you might try is an evening cruise on a yakata-bune, essentially an old-style Japanese izakaya restaurant-bar on a boat that cruises around Tokyo bay while you eat and drink. Of course one spot you must visit if coming to Tokyo is the famous Hachiko statue in Shibuya, erected by local residents to honor the dog who waited faithfully for his master to return, even after the man died.
Other random tips:
The Tokyo area is actually not that good a place to visit if you want to see cultural stuff. There are only a few choices, Nikko and Kamakura, plus Matsumoto Castle, the only truly grand Japanese castle in this part of Japan. You might do better to dispense with Tokyo quickly-ish and head to Kansai where there’s more to do.
People ask me about where to find hotels, but being a resident of Japan this is hard for me since I won’t have the same approach as visitors from outside Japan. One small suggestion would be to be wary of hotel-finding services used by foreigners, since you can sometimes end up in a traditional ryokan (or whatever) with nothing but gaijin around you. (Not that that’s a bad thing.) If you do want to try a more “pure” experience, minshuku are also something to consider.
One hotel I like in Kyoto and (Shibuya) in Tokyo is Dormy Inn, a Western hotel but nice because they have proper Japanese style baths and sauna, something I am a fan of. If going to Kyoto, I’ve posted about the “machiya” homes you can rent, which let you experience Kyoto like a local would. See details in this post.
As for the best time of year to visit, spring or fall are the nicest, but things can get crowded. It’s hard to catch the cherry blossoms accurately (they bloom from late March through early April but this can vary a lot). The time of red leaves changing in October is probably the best time in Japan, personally, and if I recall airfare is cheap during that time, too.
There’s a lot to see in the Tokyo/Kanto area, like Kamakura.