Day 1: Shimokitazawa – Bohemian Cool

Wander the narrow streets of Shimokitazawa—Tokyo’s Williamsburg—where indie shops, vintage clothing stalls, vinyl shops and independent cafés cluster around the station. 
Spend the afternoon knocking back craft coffee at a cozy terrace café, browsing rare second‑hand jackets, and inhaling the smell of old records. At dusk, slip into a tiny izakaya off Ichibangai for yakitori and shochu. This isn’t curated for tourists—it’s where young locals unload their week.

Day 2: Kōenji – Underground Tokyo

Head further west to Kōenji, home to grit, music, counter‑culture and retro record bins. Its winding streets and underground live houses host punk bands, indie DJs, and local festivals such as the Awa Odori, where you’ll witness raucous dancing and chant to traditional shamisen beats. Grab dinner at a ramshackle gyoza bar or noodle stall frequented by art students and night‑shift writers. This is Tokyo that refuses to conform.

Day 3: Yokocho Alleys & Izakaya Crawls in Shinjuku

Tonight you’re crisscrossing the back‑alley izakaya labyrinths near Shinjuku East Gate—far from Golden Gai’s polished aesthetics—where salarymen crowd smoky grill stalls and toss back soy‑dripping karaage and cheap beer in narrow lantern‑lit corridors. These yokocho alleys in Shinjuku—they’re the pulse of Tokyo after dark. Shadowy, sticky‑floor, yakitori joints rubbing elbows with office workers and part‑timers. No tourists, just humanity in full color. Then, pop into two or three tiny joints, talk to locals, graze on grilled innards, pickled radishes, and end the night at a standing bar for sake. No gimmicks, just grit and genuine company.

Day 4: Depachika Lanes & Hidden Izakaya in Residential Azabu or Tsukiji

Start with breakfast in a department store basement (depachika): high‑end bento, fresh sushi counters, pastries crafted with obsessive detail—these hidden food halls are where Tokyoites actually shop for serious lunch ingredients. Then drift into a lesser‑known residential café in Azabu or Tsukiji—no neon, just understated charm. For dinner, track down a local b‑kyū gurume haunt: think monjayaki in Tsukishima or ketchup pasta in Hatagaya, where lunch is nostalgic, slightly greasy, and deeply satisfying. Nearby, stroll around Chiyoda City’s mperial Palace. It’s simply stunning and an ode to old Tokyo.

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Wake up and head to Harajuku for coffee…served by a bear in a literal hole in the wall. Yep, do it. And the coffee is surprisingly good, though a tad on the sweet side. Then shop around on Harajuku’s Takeshita Street for a taste of Tokyo’s eclectic and creative side. 

For something more traditional, it’s hard to top (certainly in duration) kaiseki from Kiyoyasu House Roppongi. And for all of the ramen snobs out there, wait ’til you try Tsukemen at Kinryu. No, it’s not because it’s fancy. It’s because everyone from the salaryman to the punk band chorus form the same queue at lunch.

We release our inner tourists with a trip to Tokyo station…every single trip! You’ll find everything you need from souvenirs to world class sushi at the Standing Sushi Bar. Tokyo’s train stations are just better. And finally, end your night at Shibuya Crossing. Like Times Square in New York City, everyone needs to experience it once…maybe just once.