Shinjuku
Reddit's #1 pick for first-timers, and they're right
Shinjuku Station moves 3.5 million people a day, and you'll use it constantly. Stay west of the station near Nishi-Shinjuku for quieter high-rise hotels, or east near Kabukicho if you want the neon chaos. Golden Gai's six alleys hold around 200 tiny bars, most seating six people. Omoide Yokocho off the east exit serves yakitori under the train tracks until 1am. Skip the Robot Restaurant area if you want sleep. The Tokyo Metropolitan Government Building observation deck on Nishi-Shinjuku 2-chome is free and open until 10pm.
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