Trip Report: Tokyo, Kyoto, Osaka May 2024

Here is my trip report from my mid-May Japan trip. We went to Tokyo, Kyoto, and Osaka, with a pit stop in Nara. It was a great time and the weather was perfect—only two days of rain, and the humidity was not yet at full speed.

Day 1 – flew direct into Haneda from the west coast of the US. Having done the flight to Japan and other parts of Asia from the east coast, flying from the west coast is a dream, especially with no connecting flights. Also, if you can fly into Haneda do it, since it’s a quick monorail ride into the city, versus Narita which is in a different prefecture and is a longer ride. We stayed at the JR Kyushu Blossom in Shinjuku and I would absolutely recommend this if you are looking for a good hotel that is above economy level but not a bank-busting luxury hotel. It was about $400 USD a night. Having lived in NYC for a long time I make a lot of comparisons there since both Tokyo and NYC are expensive, and I cannot imagine a hotel in a comparable location in NYC as the JR Kyushu for that price. For dinner we stumbled on this chicken ramen place that was amazing. They do a beautiful chicken shio that was very memorable.

Day 2 – We walked from the hotel down to the Meji Shrine and explored that, and then strolled from there through the Yoyogi neighborhood and around Shibuya including Harajuku and Takeshita Street. Particularly memorable was the Tower Records which was so vast. That night we did this Airbnb experience that I would highly recommend. We often do these types of tours when we are exploring a new country, and frankly they are often hit or miss, but this one was a hit and I would definitely recommend it if you want an intro to nighttime eating and drinking culture in Tokyo. The host was a real character and probably needs his own TV show or YouTube channel. The tour was in Ueno which was not an area we had on our radar for nightlife, and really fell in love with the areas around the train tracks that were full of life and so many interesting places to eat and drink, with a real lively atmosphere that reminded me of places in Europe or SE Asia due to the sidewalk cafes and people outside eating, drinking and smoking. On the tour we went to an izakaya  (Japanese pub) and sampled the types of food and you drink you would get there, and there was way more food and booze than I expected included in the tour cost. We then went to a little bar and had cocktails, and finished up at a ramen place that was also doing a variation of the chicken broth.

Day 3- Back to Ueno for the Tokyo National Museum, which was great although it’s more of a complex than one museum. We only did the main Japan building, but there are actually several buildings related to various aspects of Japanese/Asian art and history. My tolerance for museums is limited so I wanted to hit the main exhibit and get out. This area of Ueno around Ueno Park is the museum/zoo district and there are lots of other attractions there. We then went to Sensoji Temple which was probably the most tourist-dense place we went to in Tokyo. I was generally put off by all the tourists and wanted to speed through this, but the shrine itself is of course impressive. There are some good food options in the area, including the usual temple street food stalls but also some streets directly to the west with lots of good options. If you find a place doing the sweet potato brûlée, give that a try if you have a sweet tooth. You can then make your way to the Kappabashi Hondori shopping district where you will find endless blocks of shopping for kitchen and restaurant supplies including beautiful knife shops and stores selling the plastic display food that you will see in front of many restaurants. That night we did another Airbnb Experience, this time in Shinjuku. The host was meh so I won’t link to it, but it did give us a nice close up view of the Kabukicho area—the host had a suspiciously detailed knowledge of the more seedy parts of that area, and it was good to understand the deal with all of the maid bars, massage places, and the places that cater to women. We then went to the Golden Gai, and after we left the tour stayed around there and went to a couple bars. I was tempted to eat at the ramen place there but couldn’t stomach the line (to be continued on that). That whole east/north side of Shinjuku station is wild and lives up to all the expectations. If you want the neon urban jungle experience, this is it. Kabukicho is particularly visually stimulating I could have spent hours just walking around staring like an idiot. We ended the night with a light night meal of curry katsu at Coco Ichibanya. This is a chain but I thought it was good, especially after a long night of drinking.

Day 4 – We did Teamlab Borderless in Roppongi. There is lots written about this elsewhere so I won’t go into it much, but I would highly recommend, totally mind blowing. For Americans who were sad to leave their weed at home, this is the closest you’ll get! We then explored Azabudai Hills which is a fancy complex where Teamlabs is located. We had lunch at Soba-Mae Yamado which was very good (get the salmon belly). That night we went to Shibuya for some nightlife. First stop was JBS Bar, which is a jazz cafe aka jazz kissa. I went here bout 15 years ago and became obsessed with this category of jazz listening bars, which is certainly the OG version of those vinyl listening bars that are common throughout Japan and now in most big cities around the world. JBS is known for its particularly ornery owner (check out the Google Reviews), but more importantly its amazing collection of jazz and blues vinyl, and his great hi fi setup. These bars aren’t for everyone, and if you aren’t into the music you won’t like it. JBS in particular has a no talking rule. After that we went to The SG Club which is fancy cocktail bar that has a faux 1930s vibe and very over the top drinks. Also not for everyone, but if you like craft cocktails this might be for you.

Day 5 – I went to a sushi lunch at Kyubey in the Shinjuku Park Hotel (not their original Ginza location). My wife does not like sushi so this was a solo lunch. I had decided not to go to the trouble of making reservations in advance of our trip, so this one was a recommendation from the hotel concierge. I’m sure sushi experts (including those on this website) could recommend better places, but I thought the service, quality, and pacing of the experience was perfect. My wife had heard lots about the Tokyo Neapolitan pizza scene, and she did lunch at Pizza Marumo in Ebisu, which she enjoyed. It was raining that afternoon so we went up to Sunshine City in Ikebukero, which was basically a dated version of the other shopping complexes around the city (I think it was the first). Then we went to a cat cafe, which was great since we were already missing our pets. More jazz cafes that night, Paper Moon in Ikebukero and Samurai in Shinjuku. I could not resist going back to the fish ramen place in Golden Gai and waited about 40 minutes to get in. It was fine, but maybe not worth the wait. Some people rave about it but it was not my favorite. 

Day 6 – We took the Shinkansen to Kyoto which was a great experience. Make sure to stop by the Ekiben store in Tokyo Station if you are passing through there so you can pick up some bento for the train ride. The Shinkansen is a marvel (and renders the Acela in the US laughable by comparison). We sent our luggage via Yamato luggage transfer, and I cannot recommend this service enough. There are posts on this sub about it. We had AirTabs on our luggage so we could track, but honestly that’s absolutely unnecessary because they never lose anything. Once we got into Kyoto and checked into our Airbnb, we explored the river area including Pontocho Alley. I’ll put a plug in for Beer Bar Miyama 162 which is a weird little craft beer bar that had a friendly staff and was playing punk music. For dinner we went to one of the many yakiniku (grilled meat) places where you can grill various cuts of wagyu beef.

Day 7 – We explored Fushimi Inari and climbed the mountain there, and then went to Chion-in temple. That took much of the day, and then we had a late lunch in the Daimaru basement which has a really good food court. For the temples, sounds obvious but I would get there early. We got to Fushimi Inari at like 8 something and it was not crowded at all. I’m personally more of slow morning with coffee kind of person, which I think is fine for much of Japan, but for places in Kyoto that are super touristed you need to be there early. 

Day 8 – We went to Nijo Castle, the castle built by the first Tokugawa Shogun, which is worth checking out if you are interested in that era of Japanese history. We then went to Omura House for the omurice which was great, and a good option if you want to have good omurice but not deal with the madness of Kichi Kichi. That night we went to Gion and stood in a long line for the Gion Duck Noodles, which was worth every minute standing in that narrow alley. The duck was some of the best and most tender I’ve ever had. Then we went across the street to Music Bar Universe which was a small friendly vinyl bar where the owner/bartender/DJ was playing random western and Japanese pop.

Day 9 – We left Kyoto bound for Osaka, but made a day trip on the way in Nara. We took the limited sightseeing Aoniyoshi train which is a retro early-1900s style. Not sure I would recommend planning around it like we did, since basically it’s a regular train but wrapped like an old one and the interior is made up to look like a luxury car from the 1920s. The ride is so short, so unless you are really eager to get some pics for the Gram, I would just skip and take a regular limited Kinetsu train to Nara. *Tip: you need to buy a regular fare ticket in addition to the limited ticket if you buy in advance. We (and other tourists nearby) found the ticket machine in Kyoto Station confusing, but if you press the help button under the monitor of the ticket machine, a little window opens and a dude pops out to help!*

Nara was fun, but also very dense with tourists. The deer are great, so if you are going because of that, it won’t disappoint and will be exactly what you expect. Again, missing my pets at this point, was happy to have creatures wandering around me. Be sure to check out Todai-ji Temple which is one of the biggest wooden structures in the world. It and its massive Buddha are impressive and worth the visit. After we left Nara we took the Kinetsu line to Osaka and checked into our Airbnb. We stayed in the Nakazakicho neighborhood which is a microneighbrhood in Umeda near the major Umeda Station hub. Nakazakicho has an area of pre-WW2 wood buildings that has recently been occupied by artists which makes it a little bohemian enclave in Osaka. It has a great look and is definitely photogenic if you want to get some nice shots of contrasting architecture. 

Day 10 – We explored the Minami District, Shinaibashi, Hozenji Yokocho, Amerikamura, and then ended in Dontomburi. This was a Saturday night and the whole place was popping. This might have been my favorite day in Japan. The arcades and outdoor drinking/eating atmosphere is very enjoyable. The covered arcades and shopping streets seem to stretch on endlessly in all directions and it’s really hard to imagine that this is a city a fraction the size of Tokyo. I probably encountered more humans that afternoon/evening than I did in the last 4 years in the US. It’s truly amazing.

Day 11 – This was a rainy day so we went to Osaka Aquarium and the adjacent Tempozan Marketplace. The aquarium is impressive and if you’ve never seen a whale shark before, I think it’s worth it. The main Pacific tank is pretty breathtaking. For dinner we went to Ramen Kikuhan which was near our Airbnb. This might have been my favorite ramen of the trip (this was bowl number 6 or 7).

Day 12 – Went to Osaka Castle first thing in the morning. The castle and its grounds were impressive, but the interior of the castle can be skipped. The castle that you see is a replica and the inside is a modern museum that in my opinion is not well designed. If you want a tick by tick multi-floor granular overview of the Tokugawa Shogunate, then by all means (or just read a book and skip the castle). The grounds are beautiful, though, and you can get some very beautiful views of the castle. That night we walked down the Tenjinbashi arcade, which is the longest covered shopping arcade in Japan (allegedly). You could spend a whole day here, and it took us several hours to make it the whole way down with stopping for food and drink along the way.

Day 13 – Flight from Osaka > Haneda > Home.

Some tips/observations

-Suica card: this was crucial to seamlessly using transit. If you have an iPhone, add a Suica card in Apple Wallet. You can load as you go so don’t worry about how much you have in there. You can very easily tap in and out of transit, and also use it at many other establishments including convenience stores. This is an absolute must.

-Cash: I found it to be a little overhyped the need to have cash. Yes there are more cash-only places in Japan than in the US/Canada, but I used my credit card at many if not most places. Definitely have cash (and a convenient place to keep the coins), but it’s not like every place requires it.

-Weather: it gets humid so be ready for that. In May it was already sticky on some days (I’ve turned into a wimp living on the West Coast where there is no humidity). Also, when it rains, you will want an umbrella and not a rain coat. I had both, and my rain coat did not get used the entire time. The last thing you want in a humid rain is a waterproof long sleeve coat, even if it’s breathable. Literally every human in Japan will be using an umbrella when it rains, so just join the masses. The umbrella infrastructure is also great—places for them at every store entry way, plastic bags to keep them in so you don’t get the floor wet, and even umbrella locks so you can leave it outside and nobody will take it.

-Hospitality/customer service: the best you’ll ever experience. I’m certainly not the first person to say this, but you will be greeted by the most welcoming and hospital people on earth. Nearly every encounter will be pleasant, and you will be amazed the lengths to which people will go to ensure you are well served. Sometimes this is uncomfortable, like when our Airbnb host insisted that she contact Yamato and have our luggage redirected so she could personally bring it to us, and then also insisted that she meet us at Umeda station and walk us to her flat, and then exhaustively explain every inch of the home to us.

-Shoes: you will be walking a lot! Plan accordingly. If you are 40+ like us, keep in mind that you can’t just walk all day and sit in backless chairs without feeling it later unless you are in super prime condition. Also, wear socks under your shoes or bring a pair in your bag if you aren’t wearing them. You never know when you will need to take your shoes off.

-Language: you can definitely get by with English only, but it would be best to learn a few words, at least hello, thank you, excuse me to start. You will also pick up a few words along your journey. If you are self conscious about speaking a foreign language, I’ll refer you back to my point about hospitality and politeness—nobody is going to give you a funny judgmental look for pronouncing something wrong, compared to what you might get in some European countries. The people are forgiving (or at least they keep their judgement to themselves). 

-Etiquette: please don’t talk loudly in public or on the train, and don’t be confrontational with people. This is a bad look and will be counterproductive to anything you are trying to do. This is actually a very quiet country. Even in Tokyo, biggest city in the world, once you are away from the main auto roads the streets are very quiet and loud talking or shouting really stands out. Enjoy the peace!

-Moist wipes/towlettes – literally every meal, even fast food, you will be presented with a moist toilette to wipe your hands before the meal. Nice restaurants might give you an actual cloth towel. Take advantage of this! As much as I disliked Japan’s addiction to single-use plastic, these are really nice and honestly I wish they would adopt this practice in the US. Bonus, on a humid day, wipe your face with the towelette if nobody is looking—it feels great!

-Food and drink: if you like whiskey drinks, get into drinking highballs. They are everywhere, even on tap some places, and are perfect when it’s hot. For convenience store food, get the egg sandwiches. In fact, get one each from 7-11, Family Mart, and Lawsons and do a comparison (7-11 is the best IMO).