Tokyo doesn’t ask for your permission. You’re all in, or you’re all out.
It’s a city of layers on layers and relentless contradictions – where $30,000 vintage Patek Philippes tick inside unassuming back-alley boutiques, and ¥500 highballs are slammed in cigarette-singed Shinjuku dive bars.
Most people lose themselves in the sprawl. You don’t have that luxury. We’re not here for the slow-burn shrines or the guide-book traps. To do Tokyo right in 48 hours, you need a hitlist that filters the chaos – marbled wagyu that ruins all other steaks, the hidden vinyl bars where just finding it is half the fun, and the round-the-clock energy that makes New York feel sleepy.
For those who value time as much as taste, we’ve trimmed the fat and pinpointed the exact coordinates where Tokyo’s legendary subcultures meet the Boss Hunting reader’s needs.
Forty-eight hours. Zero filler. And with the new threads from UNIQLO : C’s F/W 26 collection on our back.
Let’s get to work.
Boss Hunting was in Tokyo to shoot UNIQLO : C’s new Fall/Winter collection ahead of its release in Australian stores. Enclosed is our runsheet from between takes, but you can check out the full collection shoot here, featuring the PUFFTECH you need to explore a jungle like Tokyo in comfort, style, and warmth.
Day 1
9 AM: The only thing worth doing in Tokyo before 10 o’clock (while the city slowly wakes up) is the Tsukiji Outer Fish Market. Stroll the back lanes and marvel wide-eyed at the consumption of fish soup and beer at such an ungodly hour. If you’re up super early (like 5:30 AM early), give the Toyosu Market a look for the world-famous daily tuna auction.
10 AM: Get your caffeine hit from nearby Roar Coffee, then venture a few streets over to UNIQLO’s 12-storey Ginza mega store. Disneyland for normcore acolytes.
12 PM: Time to change it up and swap the high-rises of Ginza for the burgeoning suburb of Nakameguro. Daikanyama T-Site is a book nerd’s heaven on earth, perfect for a slow browse of a mind-blowing amount of Japanese and international literature and pop culture.
1 PM: Take a short walk over the river to Traveler’s Factory Nakameguro for some vintage travel merch (the line goes fairly quickly, so just suck it up). On your way out, consider Wguymafia’s $100 Wagyu sandwich – because why not? You’ll be earning it with the upcoming step count we’re going to throw at you.
5 PM: After a reset at the hotel, race to the top of the Shibuya Sky right before sunset (book ahead). Touristy? Yes, but only from this vantage point will you get a true appreciation for the megacity that Tokyo really is. Make sure the weather’s turning it on for a killer sunset, or just skip it.
6 PM: Jump straight in an Uber and roll over to Gonpachi Nishi-Azabu for dinner. The iconic diner from Tarantino’s Kill Bill heaves every night of the week, and it’s a great launch pad for the damage you’re about to do to a few shots of sake in the backstreets of nearby Roppongi.
8 PM: Stroll 10 minutes to MUSIUM, a new(ish) listening bar where you roll coloured marbles down the bar to select your soundtrack genre.
9 PM: From here, wander down the street to Bar Centifolia to watch the hall-of-fame cocktail master do his iconic work. Fire, samurai swords, glitter – it’s a whole performance. Yes, it’s about $50 AUD per cocktail, but it’s worth it for the pagentry. If you can’t get in immediately, put your name down for tomorrow night instead. Bookings only work directly at the door.
10 PM: Do your best to knock over the many bars or late-night ramen joints nearby. We were exhausted at this stage, but if you’re heading back to Shibuya, lean into the chaos until the early hours and start the second half of the evening at The Music Bar Cave.
Day 2
8 AM: Start the day with a cappuccino from About Life Coffee – ask for it extra hot, as the Japanese seem to enjoy serving them lukewarm. The banana bread here slaps, too.
11 AM: Wander through the streets of Harajuku – AMORE for vintage luxury, The Divot Store for some retro golf gear, and marvel at the architectural design of some of the quirkiest retail boutiques in the world.
1 PM: Fill the afternoon with a roam around Shimokitazawa (for a lingering Old-Tokyo vibe), or catch the metro to Nakano Broadway for a solid selection of vintage watches.
5 PM: Open the account with a takeaway ice-cold Asahi from a local konbini (convenience store) and walk around the Shinjuku area before you find yourself at The Park Hyatt Tokyo.
6 PM: Enjoy a sundowner at the cinematic New York Bar atop the Park Hyatt – famed for its background cameo in Lost In Translation.
7:30 PM: Slide into a cab or Uber to Janai Coffee, where you’ll need to rotate the bar’s logo on their mobile homepage to gain access. Even with a booking, you can’t get in unless you show the code. Look for the secret cocktail menu on the underside of your coaster.
8:30 PM: Then, pick either A10 or Bar Banten for an intimate listening bar experience. The latter hosts just six seats accessed via a secret half-door on the 5th floor of a residential building.
10 PM: Walk to Narukiyo for a late dinner – order the wagyu, edamame, and then lucky dip the rest. You won’t be reading the menu, so just hope one of the guys picks up what you’re putting down. While you’re at it, pick up and put down a few pints of Kirin Ichiban.
12 AM: Once you’re limbered up, end the night at Shinjuku Batting Centre. Bring cash, and start with the 80 km/h cages. Move to the 120 km/h cages for a laugh, then wince the next day from the aching muscles you didn’t know you were using.
Before you set off, explore UNIQLO : C’s FW collection for your new travel wardrobe here.
This article is presented in partnership with UNIQLO. Thank you for supporting the brands that support Boss Hunting.
