Tip: Chic hotels were in short supply in the area until The Aoyama Grand Hotel opened in 2020. Breaking away from the typical wabi-sabi look, it’s decidedly mid-century modern in direction and houses five restaurants including a hip rooftop bar called The Top. 

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It says a lot about a neighbourhood when it’s the birthplace of Tokyo’s first-ever boutique hotel, Claska. When it opened in 2003, Claska drew the curious and creative to this sleepy slice of Meguro and it’s become a magnet for this type of crowd since. While Claska’s doors have closed, many other cool establishments have opened, making it fantastic for a day of flanerie and window shopping. Stop by fashion label Visvim’s unassuming boutique set in an old home, stationery brand Traveler’s Factory’s shop inside a former paper processing factory, as well as cult homeware store Kinto, which stands on a quiet street.

Tip: Cover more ground by jumping on the saddle of a Tokyobike. The stylish bicycle brand offers rentals at their Nakameguro branch, and they’ve also come up with a curated insider guide to help cyclists plan their routes.

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Just 10 minutes from the madness of the Scramble Crossing in the inner reaches of Shibuya is the charming neighbourhood of Tomigaya, widely considered the trendiest district of Tokyo. Before gentrification transformed it, Tokyoites already came to relax at Yoyogi Park—a quintessential cherry blossom destination—or to visit the nearby Yoyogi National Gymnasium built by modernist architect Kenzo Tange for the 1964 Summer Olympics. Today, design and architecture lovers can find plenty of inspiring stops such as the ceramic haven of Toguri Museum of Art and popular coffee haunts like Fuglen, the Oslo-born cafe brand decorated with vintage furniture.

Tip: The much-anticipated Trunk Hotel Yoyogi Park recently opened boasting minimalist interiors by Tokyo-based Keiji Ashizawa Design and Copenhagen’s Norm Architects. It has the sexiest rooftop infinity pool in the city, which overlooks the lush treetops of Yoyogi park.

A short bus ride from Shinagawa takes you to Tennozu Isle, a former fort turned art and design district that’s quite distinct from other areas of Tokyo. Art lovers make a beeline for the Terrada Art Complex, a repurposed warehouse turned creative venue with galleries and art studios. Similar initiatives can be found on Bond Street, which is lined with old warehouses transformed into shops, bars and restaurants. Stop by Archi-Depot, a museum with small-scale architectural models and Pigment, an art supply shop displaying 4,500 colours on a rainbow-like wall with interiors designed by no less than Kengo Kuma.

Tip: Itching to shop? Head over to Slow House, a beautiful lifestyle shop stocking vintage furniture, fashion, plants, cosmetics and the Ouur brand by Kinfolk. 

The upscale neighbourhood of Daikanyama has loads of cult boutiques, stylish third-wave cafes and brunch spots, and design finds that has interestingly garnered it the nickname “Little Brooklyn”. A major draw is Daikanyama T-Site, perhaps the world’s most impressive book emporium spanning three interlinked buildings in a forest-like setting. This award-winning “library in the woods” was conceived by Klein Dytham Architecture, who cleverly used the letter T (which stands for Tsutaya), as an interlocking motif for the building’s facade. There’s also the classic Hillside Terrace by Japanese designer Fumihiko Maki, a mixed-use building constructed in phases from 1967 to 1992. The streamlined building is said to have influenced the entire evolution of Daikanyama itself.

Tip: Old mingle with the new in the highbrow district of Daikanyama. Case in point: in the midst of modern buildings is Kyu Asakura House, a traditional Taisho-era mansion with an expansive Japanese garden.

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