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top five guide: tokyo, japan

Updated: Sep 7, 2023

Tokyo River Cherry Blossoms at Night 2023

Tokyo has sat atop my bucket list for years. Everything I learned about Japan's capital city made me fall more and more in love. The food? The cleanliness? The quirks? The futuristic toilets? Truly what is not to love? It seemed like this place truly had it all, and I just could not wait to see it for myself.

Naturally, I feared that I had built up an image in my mind that would be impossible for the real Tokyo to live up to. When we arrived (just in time for an unseasonably early cherry blossom season), I was trying to temper my lofty expectations. But I didn't need to. Tokyo lived up to everything I had imagined it to be and then some. Spending a week there wasn't nearly enough for me and I hope to come back to Japan many, many times.

Here are my top five tips for a trip to Tokyo:

Shinjuku at night neon-lit street raining umbrella 2023

1: where to stay

Tokyo is the largest city in the world with the sprawl to match. There is no single "downtown," which can make it challenging to determine where to stay. I'll do the work for you: stay in Shinjuku. This vibrant area is centrally located and provides a quintessentially "Japan" experience. We found an affordable last-minute stay at The Knot Hotel Shinjuku, a medium-sized hotel on the quieter western side of the district. The chic lobby was ideal for remote working and the bakery was fantastic for breakfast each morning, though the rooms were very small (a common feature of many Tokyo hotels).

Omoide Yokocho alley Shinjuku Tokyo Japan lanterns 2023

2: shinjuku sights

Speaking of Shinjuku, there is a LOT to see here! By day, enjoy a refuge from city life in Shinjuku Gyoen Park, which is particularly stunning during cherry blossom season. By night, this area truly comes alive: start with dinner in Omoide Yokocho (pictured), a snug and smokey alley lined with izakayas. Follow it up with drinks in Golden Gai, a picturesque series of charming alleys with tiny, intimate bars. End with exploring the wild district of Kabukicho, home to Tokyo's infamous girl bars, host bars, and love hotels. Escape the wilder sights by grapping a nightcap at Bar RPM, a tiny bar for audiophiles with an extensive vinyl collection and incomparable vibe. There is hardly a night more distinctly Tokyo than this.

Two Sushi Chefs Tsukiji Market Tokyo Japan 2023

3: eats worth the wait

The good news: many of the best eateries in Tokyo are intimate, relatively affordable, and don’t require a reservation. The bad news: you'll almost certainly have to wait in line to eat there. Don't let that deter you: the line moves quickly and the food is very much worth your time (but keep in mind groups larger than 2-3 may have a hard time staying together). Our favorite spots: Ichiran Ramen (famous chain), Udon Shin (get the carbonara), Uohgashi Nihonichi Shimbashi Hibyaguchi (standing sushi bar, shockingly incredible), Fuunji, and anywhere around Tsukiji Market (pictured).

Harajuku Tokyo Japan Street Boutiques Shopping 2023

4: where to wander

First I fell in love with the food, then I fell in love with the urban planning. The pedestrianized streets, human-scale architecture, and quirky nature of Tokyo makes it true pleasure to explore by foot. Four areas we particularly loved for wandering without a plan: Shibuya (the famous scramble crossing and sky-high billboards are classic Tokyo), Harajuku (we preferred laid back Cat Street, though infamousTakeshita Street is wild), Nakameguro (a serene and upscale vibe on the Meguro River), and Shimokitazawa (a hipster enclave of vintage shops and well-dressed people).

Capsule Vending Machine Store Tokyo Japan 2023

5: only in japan

There are a few must-visit places that are so quintessentially Japan it would be sacrilege to miss. An obvious one is 7/11, which you won't have trouble finding as there are literally thousands in the city. Explore the quirky and delicious foods here, and try a packaged pancake (trust me). Akihabara is an electronics-lover's dream and the 9-floor Yodobashi-Akiba is worth exploring, especially if you encounter rainy weather. Don't miss popping into a karaoke bar, a capsule vending machine shop (pictured), an arcade, and a pachinko hall (the closest thing to legal gambling in Tokyo).

bonus: cherry blossoms

If you are considering visiting Tokyo, there is hardly a better time to do so than during cherry blossom (sakura) season, which is typically late March-mid April. The Japanese practice of hanami - the appreciation of the transient beauty of the flowers - will be on full display, and it's a beautiful sight to behold. If you visit, make sure to picnic under the trees Shinjuku Gyoen Park (book tickets in advance and get there when it opens), stroll the Meguro River Cherry Blossom Festival at night (while sipping on some pink bubbly), and take a serene boat tour by day or admire the lit up trees by night at Chidorigafuchi (pictured in cover photo).

You can't always do it all, so one thing we didn’t do but wish we had:

Have an omakase experience. We focused primarily on enjoying many cheap (and delicious) eats across the city, but we would love to splurge on a Michelin-starred omakase experience on a future trip.

Have a great trip! Feel free to leave a comment with your own favorites. You can also find these recommendations (and more!) in map format by following me on the Out of Office app.


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