You can get a quick and cost-effective feel for a city by planning in a layover when you book flights. It just depends on how much of a hurry you’re in and how the routes work. For example, I planned time in Tokyo on a San Francisco-Hong Kong flight that had an overnight plane change at Tokyo Haneda airport, arriving at about 3pm and departing at 9am the following day. Haneda is really efficient (check your visas as ever, but for the most part it is stamped visa on entry) and about 30 minutes into town on Tokyo’s superb metro, so it seemed worthwhile. I even managed to fit in a work meeting on the day I arrived.
I decided to stay in the Shimbashi neighborhood, which only required one train change from Haneda by metro (Tokyo Monorail to Hamamatsucho then change to Shinbashi). Tokyo’s metro is cheap and efficient; at Haneda they have English-speaking staff standing by the ticket machines who will tell you which ticket to get and point you in the right direction.
I stayed at the Sotetsu Fresa Hotel, about 5 minutes’ walk from the Shimbashi metro station. For about US$100 I had a great and compact room, which included a breakfast I wasn’t able to have given the 08:55 plane departure the following day.
Shimbashi is a good place to start with Tokyo’s many neighborhoods – just south of the Imperial Palace and Ginza areas, it is central and downtown but still very local, even if many of the people are tipping out of the offices on a Friday evening. I went to the Toridori restaurant just west of the Shinbashi metro on Japan, on 2 Chome−15, which had a great range of izakaya type options.
There are plenty of restaurants and izakayas in the area as well and it seems that pavement drinking is approved of.
Craft beer culture has arrived in Tokyo, with many excellent Japanese micro breweries featured. I liked the Craft Beer Market in Toranomon.
Finally you can just go for a wander round the streets and observe.
And then back on the metro early the following morning for the 30-minute journey back to Haneda.