I've studied Japanese for the past 10 years, had the opportunity to live and work in Tokyo, and one of the things I get asked a lot is for recommendations for the city. I love food and I love walking. Below is a quick list of wonderful spots for both of those things; definitely a good list of places to take a walk to should you find yourself in Tokyo!
Bars
Bar Martha
This is not a normal bar. The atmosphere is distinctly western, but the quality and attention to detail, from their snacks to their extensive cocktail menu, to the truly audiophile-level speaker system and record collection, this bar is very Japanese. The music is never live, yet this is known as one of the best blues and jazz bars in Japan; the speakers are really that good.
Ren（蓮）
You will not find this place on Google maps unfortunately. It is well worth your time getting lost just trying to find this bar. It is located in the famous Nonbei Alley（のんべい横丁）, a tiny alley filled with small 4-8 person bars, right outside the main Shibuya station（渋谷駅）. It will be the very first sliding door to the right when you enter the alleyway. It is right next to the tiny outdoor washroom. It has enough room for 5-7 people. It opens at 6pm and closes at midnight. Your best bet is to go their early, around 6-7pm, and make a reservation in person for later in the evening, then take a stroll around the Shibuya and Harajuku area until then. If you mention my name or face (Brian), Sachiko-san, the owner and manager is sure to treat you nicely. She still remembers me after years.
Location here.
Matsusō（まつ惣）
Coming across this place made me feel like I had stepped onto a movie set. Walking with no particular place in mind, we heard the voices of old men singing within an outside enclosure. We peaked inside and found a large group of 20 or so men in their 70s downing drinks and singing in unison, school songs and odes of a past time. After talking to the owner, we learned that he was university friends with all of the other men. They had all been in the choir together. Even after 40-50 years of friendship, they all found time at least once a year to come together at this little bar to have snacks, drown in drink, and sing merrily together. Seeing friendship that strong and everlasting was something special. They have amazing things to snack on and a beer’s a beer, so this place is no doubt a good spot.
Location here.
Random Food Notes
Find a curry place and get Ton-katsu curry （とんかつカレー）. Most any place should do. You will thank me later.
Save any ramen（ラーメン）for the end of a night out. It's what all the cool kids do and you are sure to meet some nice people in line or around your table.
Kome-fuku（米福）
This is, like most Japanese places, not very big. It's located downstairs. You will want to make a reservation. This is a great place to go in Tokyo if you want to experience top of the line Japanese cuisine. It will run anywhere from $70~200 a person, mostly on what kind of drinks you get. My recommendation is to select one of the course meals. It's a real experience.
Walking spots
Omotesando（表参道）
This spot is the main high-end shopping district. Walking into the clothing shops is fun, yes, but the real treat is checking out all the people walking around this area. A lot of people have amazing style in this part of town and in my experience, some of the most amazing stuff people are wearing might be designed by the person; very good spot to talk to people and learn about what they're doing.
Harajuku（原宿）
This spot gets a bit of a bad wrap because of its association with all the anime nerds. But there is another side to Harajuku, referred to as inner-Harajuku（裏原宿）, which are essentially all of the alley ways that are off of Omotesando. Inside these winding streets, you will find an endless supply of specialized thrift shops - everything from nostalgic 80s and 90s fashion to hipster apparel and high-end second hand garments. There are also plenty of great little boutiques by local designers; lots of styles you can only see in Tokyo. It's fun to walk into stores around this neighborhood as the people working there tend to be engrossed in their work and love to talk about it all.
Kōenji（高円寺）
Kōenji is really not a well known spot at all. It’s a bit off the beaten path; not even on Yamanotesen（山手線）. But resting inside the streets of this neighborhood are some of the more eccentric second-hand stores and at much more reasonable prices compared to some of the shops around Harajuku.
Galleries
Design Festa Gallery
This large gallery is actually about three or four galleries in one. It’s nestled in a deep corner of inner-Harajuku. Depending on which side you have the pleasure of entering from, you will either be met by abstract pipe art handing from a white facade or you will be met with a wide open photography gallery. The galleries are always changing, so it is not easy to say what this place specializes in, but each gallery space is very different and the entire place can come across as amateurish at times to high-brow and even avant garde. Site here.
Dee’s Hall
This gallery does a nice job straddling the line between pieces you could easily enjoy placing in a home, while also being distinctively artistic. While I was there, they had an exhibit focused on carved wood pieces, but it seems they also dabble in ceramics, paintings, and sketches. Site here.
Coffee Shops
I don’t have much to say about each individual coffee shop. These are just a few I thought had some tasty coffee.
About Life Coffee Brewers location
The Local Coffee Stand location
Streamer Coffee Company location