We meet one stop away from Shibuya, in the quieter Daikanyama neighborhood. Mai’s husband works at our first stop on the tour, Bench at the Greene, a small shop carrying a well-appointed selection of menswear from the US and Europe. Next, through a maze of small streets lined with even smaller boutiques we reach one of the area’s main attractions: the Tsutaya bookstore. Or better put, megastore. Consisting of three two-story glass cubes interconnected by walkways, each structure is the size of a regular bookstore. Here one can get lost in the mountains of various media, new and vintage. Flanked with cafés, restaurants, a dog spa, and a bike store, the surrounding area has the feel of a small village plaza: family friendly and less hectic than Tokyo’s main shopping districts. We see a lot of young families with children—lots of baby strollers—and lots of pristinely groomed canines.

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After a chat with friends and a quick coffee, we decide to try our luck with public transportation on our way Harajuku, the busy shopping area close to Yoyogi Park. While it has been a center for independent youth fashion since the mid 1990s—brands such as A Bathing Ape, Neighborhood, Stüssy and X-Large opened their first boutiques here—, since the mid 2000s, Harajuku has also been attracting upscale retailers such as Polo Ralph Lauren, Chanel, Prada and Bulgari. These newcomers now occupy impressive spaces along the main avenue, Omotesando.

But before diving into the throngs of shoppers, we power up at a small American-style diner called Golden Brown in the Omotesando Hills luxury shopping mall. What at first might seem like a contradiction—burgers and luxury goods juxtaposed—turns out to be perfectly matched. Everything about this place is as immaculate and well considered as the surrounding boutiques. If you are looking for the city’s best hamburger, this is where to go.

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Now, we need caffeine—and are looking to watch of the sunset from an elevated viewpoint above the city. Mai suggest we head to Bills Café on the roof of Tokyu Plaza near Harajuku Station. Up there, we also get a novel view of the masses of Sunday shoppers, flowing in all directions. It is clearly a much younger crowd than in Daikanyama. While Takeshita Street belongs almost entirely to teenagers, Omotesando and its side streets are populated by affluent shoppers in their mid twenties to thirties. There are fewer families and hardly any people over fifty.

In the last hours of our Sunday field trip through Tokyo, Mai shows us her favorite boutiques close by, many of them newly opened. She mentions that this area has seen recent changes. Some of the original Ura-hara (‘back streets of Harajuku’) retailers have moved to Shibuya, Mai’s other choice for shopping excursions. Unfortunately, however, we have to call it a day. Baby Zooey is getting just a little cranky now—she has been the most pleasant assistant tour-guide all day—and our energies are running low as well.

But, we will meet up with Mai again for the third and last part of this feature. She will share with us more about her daily life and mobility in Tokyo.