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The coolest places in Tokyo

From its street fashions to its trendsetting tech, its modern architecture to its neon-doused nightlife districts, Tokyo is a famously cool city.

But it’s also a sprawling metropolis, and you’re as likely to find yourself lost in a maze of residential streets or wandering past nondescript office buildings as stumbling upon a vintage clothing store or chic café.

To help you out, Rebecca Hallett s compiled a list of some of the coolest places in Tokyo. From major attractions to off-the-beaten-track spots, each one will show you a different side of Japan’s capital of cool.
1

Cat Street

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Meandering from frenetic Shibuya to fashionable Harajuku, Cat Street offers a laid-back experience of this trendy district. The tree-lined avenue of Omotesando may be the go-to destination for big-budget shoppers, and the crush of Takeshita Street pulls in fans of kawaii and only-in-Japan street fashion from all around the world. But it’s the independent boutiques, quirky cafés and tiny galleries of Cat Street which truly reflect the creative core of this fashionable part of the city.
2

Yayoi Kusama Museum

credit: Raquel Moss / Unsplash
This sleek, white five-storey building on an unassuming street in Shinjuku provides a light and airy backdrop to the often colourful, bold and visionary works of one of Japan’s greatest artists, Yayoi Kusama. The exhibitions change twice each year, and as you have to book tickets in advance, you can be sure that you won’t end up with crowds blocking your view of the remarkable artworks. These might include small etchings or large-scale paintings, sculptures or immersive installations like Kusama’s beautiful, unsettling mirror rooms.
3

Nakameguro

credit: Watcharawich Jirawongsapan / Dreamstime
This sophisticated neighbourhood bursts into colour each spring, when blooming cherry trees encase the Nakameguro River in a tunnel of soft, pink blossoms. But the area is worth a visit in any season, just to stroll over its bridges, stop off at its vintage shops and pass the time at its European-style café terraces. It’s also home to the largest Starbucks in the world, the Kengo Kuma-designed Reserve Roastery – definitely in a different architectural league to most of the chain coffee shop’s other locations.
4

Shibuya Sky

credit: Aleksandra Watanuki / Dreamstime
The scramble crossing at Shibuya is certainly not a hidden gem. It’s one of Tokyo’s best-known and most crowded spots – but that’s precisely what makes it so remarkable. From buskers to school kids, fashionistas to photographers, everyone congregates here, and there’s no better place to get a sense of how vast and varied the city is. Opened in 2019, Shibuya Sky offers one of the best vantage points of the crossing. The 360-degree observation deck sits at the very top of the neighbourhood’s tallest building, Shibuya Scramble Square, giving you a bird’s-eye-view of hundreds of people swarming over the crossing 229 metres below.
5

Shimokitazawa

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Though it’s only a few stops from Shinjuku and Shibuya, Shimokitazawa has an entirely different feeling. Even as its cool credentials have become common knowledge, the neighbourhood has maintained its relaxed, low-key atmosphere and independent spirit. It’s one of Tokyo’s prime vintage shopping destinations, and is also known for its many and varied cafés and bars. The Shimokita nightlife scene is one of Tokyo’s most diverse and welcoming, dominated by rooftop DJ sets and small-venue live shows rather than glitzy lounges and mega-clubs.
6

MORI Building DIGITAL ART MUSEUM: teamLab Borderless

credit: Luca Florio / Unsplash
Odaiba is known as a kid-friendly part of Tokyo, with its ferris wheel, entertainment complex and futuristic architecture. But teamLab Borderless turns adults into big kids, plunging them into an immersive and interactive artistic world. Wander freely through the 10,000-square-metre space to experience rooms filled with digital forests and waterfalls, golden lamps seeming to float in mirrored walls and floors, and a tea room where even the drinks are part of the art.
7

Golden Gai

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Shinjuku is known for its busy streets, giant billboards and skyscrapers. So you may be surprised if you stumble onto this area of low-rise, slightly scruffy buildings crowded around narrow streets. But what you’ve found is actually a Tokyo institution: Golden Gai, six alleys crammed with around 200 tiny bars. And when we say tiny, we mean tiny – some only fit four or five customers at a time. Most of them are themed in some way, whether subtle nods to jazz or what looks like an explosion in a toy shop. Explore and prepare to make friends with other drinkers through sheer proximity.
8

Akihabara

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Whether you think Akihabara (or “Akiba”) is cool or not is strongly dependent on whether you think geeks are chic – because this is otaku central. For gamers, anime fans and manga lovers it’s heaven on earth, a whole district filled with arcades, tech stores and themed cafés. Wander the neon-lit streets to immerse yourself in Akiba’s glorious geek culture, or stop off at one of the many arcades for claw machines, dance games, driving simulators, purikura photo booths, and much more.

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