I can not begin to explain Tokyo’s train / subway system — I don’t really know it well. However, the Yamanote line is a common one you’ll take and helpful to use for orienting yourself within the city and the Tokyo train system. It is a large loop the goes around to many of the major parts of Tokyo. you can use your Japan Rail Pass on all JR trains, including the ones in Tokyo, of which the Yamanote line is one.
NOTE: the following information is out of date. The wholesale fish market ay Tsukiji has closed and moved to the new, modern Toyosu Market (see below link). I believe the outer market at Tsukiji, with restaurants and stores, is still open.
Tsukiji is arguably the largest wholesale food market in the world. It is particularly known for its fish auctions but also sells every a bewildering array of other comestibles. The market will be moving to a new facility next year, so you won’t be able to experience it in present location much longer. I’ve sadly never been but have heard great things about it. One note: you have to go very early: check your guidebooks, but I’ve heard 4am. The common thing is to go to see fish auctions then wait in a long line at a one of the tiny sushi shops for breakfast sushi! Again, check your guidebooks.
Ginza is the 5th Ave of Tokyo --- IMHO, it is much nicer. It is very expensive, but I really enjoy walking around looking at the people and the architecture of the high-end Japanese and international retail brands. It is not nearly as crazy as 5th Ave either. I find it more relaxing than other parts of Tokyo, though it is still a vibrant shopping district.
One of my favorite things to do in Ginza is visit the basement of Mitsukoshi department store. The entire store puts US department stores to shame, and the basement is the food level. I have literally cried when i first visited the downstairs; the variety and quality of everything is awe-inspiring — no pictures allowed, unfortunately. You’d likely go broke building a full meal here, and I don’t recall if there are samples; however, you can pick up a small picnic lunch or snack to fuse the sense-memory in your brain.
I’d also highly recommend arriving before they open, which i believe is 10am, so try to get there at 9:45-950a. The store employees line up at all the doors and, promptly at opening time, bow and welcome you inside. It is an added bonus experience before taking the escalators down to Japanese food porn.
Itoya is an enormous stationary store in Ginza. Japanese are fanatics for all things stationary — paper, pens, etc — and Itoya is arguably the mecca for this sort of stuff. if you’re in Ginza, this is definitely worth a visit.
Ginza is home to Kabuki-za, which is the national Kabuki theater company. Kabuki plays are amazing, and the theater provides extremely well produced translation devices timed to the performance making it is easy to follow along and understand the context of the play. You can purchase same-day tickets for one-act performances, which I have done in the past. Traditional kabuki performances are multi-act and can last half a day, but they also perform these single-act shows to be more digestible to the masses. Regardless, they are a memorable experience.
harajuku & omotosando
Harajuku is epicenter of “Tokyo street fashion”. It is very busy and very touristy but can be interesting if you want to see kids dressed in the craziest outfits.
Omotosando is nearby and, IMHO, is sort of a sister region to Ginza. Ginza is an older, more expensive clientele, while Omotosando is younger and more design-oriented. Energy is completely different to Harajuku; it is much more mature. The main drag of Omotosando is interesting, but i also like to aimlessly stroll through its side streets.
Shibuya is sort of the Times Square of Tokyo. It is much better than TS yet I personally still don’t like it too much. That said, you sort of have to visit, if only to see the famous “scramble” street crossing. The rest of the district can be pretty crowded but worth a bit of strolling around. It can get a bit disorienting, though.
If you happen to be in Shibuya at night, when it is most interesting, i might recommend JBS (Jazz, Blues, Soul). It is a small record bar tucked away on a nondescript Shibuya street. It is not horribly hard to find, though it is on the second floor of a rather generic building on a side street. Look for “2F - JBS” on a small office directory on the building.
I believe the proprietor sells no food and only limited selection of drinks. It is a reasonably cool place to chill for an hour or two. You will find most of the clientele are ex-pats, which is something I typically avoid, but the extensive jazz-blues-soul vinyl collection more than makes up for it.
Yoyogi Park is snuggled to the northwest of Shibuya and Harajuku / Omotosando. It is a very nice park, which was famous decades ago to see groups of kids dressed in themes, like rockabilly or punk rock or Elvis etc. Not sure they still do that but have heard it is a nice place to visit, especially if you want to escape some of the craziness of Shibuya or Harajuku.
ueno & Ya-Ne-Sen (Yanaka, Nezu, Sendagi)
Ueno park is notable for a complex that contains the national zoo, a large lotus pond, and several national museums (science, art, history). Ueno park is easy to get to and around; the scale of everything is less overwhelming than many other parts of Tokyo; you can easily stroll around and relax without being caught in sea of people or glass high-rises. A lot of people really love Ueno, and you’ll see many tourists; however, I simply find it ok — it is exceptionally nice during cherry blossom time (spring). I personally enjoy it simply for its low-stress vibe and easy people-watching.
That said, the main reason to visit Ueno, IMHO, is as a gateway to the adjacent YaNeSen district, which is one of my favorite areas of Tokyo. Ueno is easily accessible via the JR Yamanote line, and YaNeSen is easy walking distance northwest of Ueno.
This zone can be considered one of several “Old Tokyo” districts. Like NYC, Tokyo has people born-and-bred there as well as transplants from other cities. Old Tokyo areas like YaNeSen are traditionally multi-generational Tokyo-folk, so, while very Japanese, it is also very Tokyo. This Old Tokyo is sometimes referred to as Edo-style; the Edo period was ~1600-1850, and “Edo” is the old name for “Tokyo”.
The area is very cute, rather quiet (for a big city), the streets are windy, and populated by two-story buildings, many with businesses on the ground-level. Recently there has been a bit of renaissance to the district whereby graduates of art universities take over a neglected building and convert it to a nice cafe, restaurant, beer pub, hotel. This may seem like gentrification but these kids have done a great job of revitalizing an interesting historic district; there’s plenty of traditional businesses to keep the old flavor.
I like to simply wander around the streets of YaNeSen, but three notable places are: Kayaba Coffee, Yanaka Cemetery, and Yanaka Ginza. You can stroll north of Ueno park and stop at Kayaba Coffee, then continue up past the cemetery, followed by Yanaka Ginza.
This is a classic example of former art students converting an old building to something very nice. They have small meals and good coffee house fare. the "tamago sando" (egg sandwich) is extremely good. They also have a bakery, which is new since the last time I visited, and may be in a different location; I’m referring you specifically to the cafe.
You don’t have to actually enter the cemetery (unless you want to); rather, just stroll past it via a long road enroute to Yanaka Ginza. The walk alone is wonderful as you pass the old gravestones; the vibe is very peaceful while mildly spooky.
This is an old outdoor shopping district. It has become more touristy and a bit kitsch in the last 5+ years, though I still feel it warrants a visit. There are many cute specialty shops and yummy (“oishii”) things to snack on. The street itself, if I remember correctly, isn’t super long.
You can access many tokyo subways from this area, if you want to head somewhere else; or, I might suggest heading back to Ueno station via an aimless stroll through the northwest side of YaNeSen. You basically can get to the end of Yanaka shopping district, then head left and wind your way back to the station — just look on the map periodically. It should add maybe 30 minutes, and there is not any particular points of interest along the way, but you’ll likely stumble across a cute shop or cafe nestled among the small houses. One place you could head to specifically is Nezu Shrine, which is on the northern tip of Tokyo University. This is all basically on the way back to Ueno Station, though may take you a bit out of the way.
Also, if you feel like you want to get back on Yamanote Line from Yanaka shopping district, then there is also the Nippori station relatively near the east entrance to the shopping zone.
One last recommendation is the following hotel in YaNeSen.
Hanare is like Kayaba Coffee in that former art students took over some old buildings. Uniquely, this hotel is actually a couple of older buildings that, converted, combine to one small hotel complex. Their idea is that "the whole town is your hotel” in that the rest of YaNeSen serves as an extension to the hotel.
Hagiso is a cafe / bar / shop; the the main hotel lobby is located above. Marukoshiso is the sleeping quarters, which is renovated local houses.
I have yet to stay but have seen it highlighted on Japanese TV. It looks very cute, very Japanese, very Tokyo, very modern yet very “Edo” as well. I believe the bathrooms are shared, and they include a shower, but you are also provided with a ticket to “sento”, which are Japanese communal baths. Sento is sort of like "onsen" (natural hot springs) in that it is shared place to bathe, but this is typically not natural spring water. You do not have to partake, but it is a free option included with the stay. (breakfast is included as well).
Akiba is “Electric City”, the electronics retail capital of Tokyo, Japan, and arguably the world. I personally feel this is a must-see district in Tokyo since it encapsulates a lot of the craziness of modern japan. There are massive retailers, such as Yodobashi, which you should try to visit simply to see the dizzying array of products available to the Japanese market. There are tons of little specialty shops in side alleys; some sell tiny bits of electronics (fans, motors), while others specialize in super-high-end equipment (stereos for example). There are also lots of people walking around in costumes; you’ll likely see many “maido”, girls dressed up like trashy maids. Go to the district, roam the streets, pop in a few stores. Like Shibuya, Akihabara can be a bit more interesting at night, when it is all lit-up, though it is fine during the day to, if that is how your schedule falls.
This area is a bit out of the way in Tokyo. It is a small urban island in Southeast Tokyo. Depending on where you are at the time, it can be a short subway ride, but it is a tad remote compared to most of tokyo.
I recommend Tsukishima mainly for “monjayaki” (or simply “monja”), which this district is famous for. Read the very short description of monja in the wikipedia page below. It is often talked about in contrast to “okonomiyaki”, a more well-known “savory japanese pancake”.
Basically, you sit at a table with a grill (“teppan”) on which the waitress dumps a mix (depending on what you order) of vegetables, egg, meats, seafood, cheese, and a slurry. She then performs a magic act that, over several minutes, turns this odd concoction into a yummy (“oishii”) carmelized pancake-like dish. You and your dining companions then cut-up and eat via provided small spatulas (“hera”). Note: you can do the cooking yourself, but the waitresses are happy to do it and experts. Mentaiko, spicy cod roe, with cheese is a popular combination.
Besides enjoying monja itself, i like the vibe of the places in Tsukishima. It has a very local feel, and everything is small scale — buildings are rarely more than 2 stories, shops are very small. The communal aspect of the teppan in the middle of your table, and groups of locals eating and drinking around you makes for a nice experience.
If you decide to make the trek, I’d recommend the following restaurant. It is chosen solely because it was one of the few non-smoking places in the area — food cooking at your table is enough smoke! Regardless, i enjoyed their monja.
Aside: you’ll likely tire of the lack of non-smoking establishments in Japan. It is almost a joke where most restaurants and cafes have a non-smoking section, but really it is a tiny zone without any environmental isolation from the smokers.
Grand Sumo tournaments happen six times throughout the year, and only three are held in Tokyo. A tournament runs for two weeks, Sunday to Sunday. It is best to purchases tickets well in advance, particularly for weekend matches, and even more so for a tournament's final days. If you are unfamiliar with the sport, I'd recommend finding a brief primer since it will greatly enhance your enjoyment of viewing it live.
Sumo matches happen throughout the day, starting around 08:00 and ending around 18:00. Each set of matches is for different rankings, in ascending order: the earliest is of the lowest ranks, while the last set of matches are among the top wrestlers. You can go in and out throughout the day; however, you’d be more than fine attending only the final set, which starts around 15:30 going until 18:00. The set before (14:00-15:30) can also be quite good.
At the beginning of each set of matches there is a formal procession of all the wrestlers dressed in ornamented garb; try your best to catch this as it is visually interesting — the final set’s procession is around 15:40. There is often a short ritual at the end of each set, too, which can be fun to watch as well, though most Japanese will be filing out of the stadium.
I’d recommend going early enough to see the main wrestlers arriving at the stadium. They are dressed in “yukata” (light cotton kimono) and gradually file in from the street to a side entrance. My recollection is that if you’re looking at the front of the stadium (Ryōgoku Kokugikan), then they walk up the side street to the right. It should be fairly easy to spot, as there will be a long line of japanese people gawking and cheering mild encouragement. I estimate this happens gradually around 14:00While this happens outside, you might actually need your ticket as there may be some security you have to pass even though you haven’t yet entered the building. I don’t recall exactly but just a note in case.