I’m no expert, but I’ve visited Japan three times now for 2 weeks each time so I hope I can be helpful.
Food
If you want fast food, what you’re looking for is gyudon places. They sell protein over rice for very cheap prices and are open 24 hours a day. My favorite one is Sukiya.
If you want to go to a specific restaurant, I recommend beginning to plan 3 months in advance. Otherwise starting a bit over a month in advance should be sufficient. Unfortunately for me, Japan plans ahead of time very well.
Reviewers are very harsh in Japan. Use Tabelog (Japanese Yelp) to get food reviews - don’t rely on Google Maps exclusively. A 3.5 on Tabelog is the equivalent of 4.5 on Google Maps in New York. A 4.0 means you’ll forget your name after eating that meal.
The average level of food quality in Japan is incredible. You’re unlikely to have more than one bad meal on a two week vacation. If you walk into random places, you’ll find decent food.
Foreign food is great, especially French and Indian. French food in Japan can rival French food in France since many of the chefs train in Paris and then return to Japan. If you find a French pastry shop in Japan I highly recommend stopping in. Stay away from Thai and Mexican though.
Convenience stores are everywhere. Please understand and take to heart that you will not get sick from the food there. The food is likely at least decent and is freshly made. My personal favorite is 7-Eleven for their food, but Family Mart has great fried chicken and onigiri.
Shopping
Japan is a fucking great shopping destination. Even if you’re not big into shopping as an activity, I recommend you plan at least a little bit to hit stores that appeal to your particular interests. The Japanese have mastered the art of creating niche products that scratch your particular itch. My pet theory is that this is from the lack of economic growth, which created zero sum competition for consumer attention. In any case, you’re far more likely to find some cool stuff than in America for some reason.
My first recommendation is Hands (formerly Tokyu Hands). It’s nominally a DIY store, but it’s more of an everything store. The Shibuya location is 7 floors of intensely well designed products that range from very useful to “but why”.
It’s also a great place to get gifts for people. I like buying things that are actually useful as souvenirs. I recommend the umbrellas, which are nigh unbreakable. Mini umbrellas are fun and they can get as light as 80g.
Japanese stationery has become exceptionally trendy in the States and for good reason. I’ll leave it to you to find a store, but Hands has a good selection.
Do note that if you get appliances they’re built for 100V, which may not end up working in America, despite the plugs being the same.
There are so many hobby shops. If you have any hobbies like model trains, painting miniatures, photography, or something else, do yourself a favor and seek out those stores. They’re intensely interesting in Japan since there’s a pretty big niche interest scene there. I’m not sure if it’s because your average Japanese consumer is more likely to spend money on such things but the hobby shops are much cooler than in the States.
Gashapon are ubiquitous but easy to ignore. Do stop by at least a few of the larger collections of coin operated machines. Even if you don’t get anything you won’t regret your time spent there.
Japanese camping supplies are quite fun. If you’re outdoorsy I can recommend checking out Montbell, Snow Peak, or a general outdoors store. I don’t think it’s much cheaper than in the States though, so this isn’t a must see.
Daiso is much more based there. I think they bring their stock of shit that didn’t sell to the American stores. It’s both cheaper and more interesting in Japan. I got a pair of collapsible chopsticks and a campfire bread toaster for under $3 total.
Clothing is generally higher quality and lower priced than in the States. Uniqlo is good for stocking up on basics - they’re substantially cheaper there and they have different stuff. Go up one size.
Japan also has a great menswear subculture. It depends on what you want precisely, but United Arrows and Beams are worth checking out. There’s also an incredible trend of Japanese companies replicating 50’s to 80’s American clothing with correspondingly high quality. I got myself loopwheeled (60’s era high quality manufacturing technique) t-shirts for around $30 each from Whitesville. The Real McCoy’s and Hinoya are two stores that you could check out. Japanese denim falls into this category.
Tabio has the best socks I’ve ever worn for under $10 a pair. They’re much cheaper than buying from the Tabio US site. Many thanks to Dio for the recommendation.
Don Quijote is a quirked up dollar store. They’re open 24 hours and have tons of fun cheap crap. Each location has different stuff since the local staff decide what’s carried in that particular store. I recommend finding a Mega Don Quijote for a larger selection.
If you want to buy some expensive crafts or artisanal stuff check out the Monocle guides to various Japanese cities. The author is very opinionated and provides cool recs.
Etiquette
Don’t do Mario Karting in Tokyo. Everyone will hate you and it’s dangerous.
Taking shoes off in public is very common. Don’t do what I did and bring socks with holes. People will generally tell you when to take shoes off so don’t worry too much about that.
Many restaurant workers will not want to be photographed. Ask before taking photos. Photos of food are okay in my experience.
Quick Tips
You can ship your luggage overnight between hotels in Japan. Not only can you do this, but you absolutely should do this. Shipping a suitcase between Tokyo and Osaka should cost below $20. Don’t be that guy dragging two suitcases during rush hour because you were too cheap to ship. If you give the address of your next hotel to the concierge, they’ll be more than happy to do everything required to ship your luggage - including calling ahead to the next hotel. Please familiarize yourself with Shinkansen luggage rules.
Japan uses tap cards for the trains. They’ve run out of the integrated circuits for these cards as of October 2023. The workaround is to add the card to your phone wallet and then recharge with a non-Visa credit card (works with Amex).
If you want to go off the beaten track, literally just go outside of Tokyo, Kyoto, Osaka, Nara, and Hakone. Those places get a lot of tourists, but as soon as you go somewhere else you’ll likely be the only tourist in sight.
You can get a JR Pass to get cheaper train travel. Use an online calculator to see if it’s worth getting for your itinerary. Note that you need to buy it outside of Japan.
The rice diet can get you a bit clogged. I recommend 7-Eleven cabbage packs.
Staying at a ryokan (Japanese inn) with an onsen (hot spring bath) is a must. It’s a quintessential Japanese experience and you won’t regret it. Ensure that the onsen uses natural spring water from nearby and not tap water - it should state this explicitly on the hotel’s website. Jalan.net is good for reviews - use Google Translate.
Get either portable wifi or an eSIM. You’ll be using Google Translate a lot.
Dormy Inn is a Japanese hotel that Japanese people stay at. If you want something a little different that’s also pretty affordable - I can recommend it. Free noodles in the evening and they have a hot spring bath (filled with tap water) on the top floor.
Japan loves trains and so do I. If possible, book a sightseeing train - I enjoyed the one between Kyoto and Nara. They also have train related souvenirs which are awesome.
Specific bits of Japan I really like
Japan has a specific brand of thoughtfulness and creativity I don’t see elsewhere as much. I’ve listed a few examples below.
dB meters on construction sites
Clear umbrellas (sold pretty much everywhere)
Standardized showerhead temperatures
Clothing at konbini (Family Mart has shockingly good quality clothes)
Numbered exits at train stations
Urban Design
I love Japanese urban design. I’d like to bring your attention to a few unique and great things Japan has.
Tiny bars & restaurants. There are so many bars that can only fit like 5 people and the owner. It leads to fun moments that you couldn’t have anywhere else in the world.
Weird shops. Rent is relatively affordable and there are relatively fewer zoning restrictions on small shops so you get places that make you say “how can you possibly afford to stay open”. The place shown below just sells handmade tea caddies.
Walkable streets
Street plants. Many people will put potted plants outside their home as a makeshift garden to make the street more pleasant.
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