Tokyo is often portrayed as a city of the future, with clean lines, capsule hotels, and vending machines at every corner. But the Showa era is everywhere if you know where to look: in the smoky yakitori alleys of Sangenjaya, the shotengai that time forgot, the small counter Hirayama drinks at in Perfect Days. The city’s most compelling spaces today are the ones that hold both eras at once.
First Day
Fly into Haneda for the easiest landing and check into Aman Tokyo in Otemachi, set across the top floors of the Otemachi Tower with views over the Imperial Palace gardens. Drop your bags and take afternoon tea in the Garden Lounge before the day starts properly.
Spend the late afternoon in Kappabashi, the strip behind Asakusa where Tokyo’s restaurants come to outfit themselves. From mom and pop stores to established brands like Kama-asa, half a mile of shopfronts with unique knives, copper tamagoyaki pans, donabes, and convincing food replicas wall to wall.
After Kappabashi, walk ten minutes east to Senso-ji, Tokyo’s oldest temple, sharing its grounds with the quieter Asakusa-jinja shrine next door. Walk Nakamise-dori between the two great gates, pass under the giant red lantern at Kaminarimon, and take in the incense at the main hall. The whole quarter has the feel of Tokyo before the highrises.
Make your way to Asakusa Station. Down the steps and into the underground arcade home to a small counter restaurant Hirayama drinks at in Perfect Days. Retro signage, patinated wood panels, and lighting that hasn’t changed in decades. Some places are appreciated just by passing through.
Head west to Shinjuku for the vintage camera shops. Film bodies from every decade behind glass, Y2K digicams stacked on shelves, and the wondrous bargain bins where you might find a gem.
For dinner, make your way to Tanbo Yoyogi. An established teishoku restaurant serving seasonal sets with grilled fish, simmered vegetables, miso soup, and house pickles. The kind of meal that makes you appreciate how Japan can make rice the headline.
Second Day
Start the morning slowly. Take the Fukutoshin line to Tas Yard for brunch, a quiet cafe tucked into a side street. Order the thick-cut French toast, golden and custardy in the middle, and coffee jelly: cold brew set with gelatin, served with cream and syrup on the side. Not too sweet.
From Tas Yard it’s a few minutes south to the great torii gate of Meiji Jingu. The shrine sits inside a hundred-acre forest, planted with 100,000 trees from across Japan a century ago. Follow the gravel path, avoiding the center reserved for the kami, past the kazaridaru (a wall of stacked barrel offerings from sake brewers) and on to the main shrine.
Lunch is Mawashi Sushi Katsu, up in the Seibu department store. Every seat has its own touchscreen, and behind it a deep menu of Tokyo’s freshest seafood. One tap and the plate rides the belt over. A three-piece otoro sampler, seabream sashimi, conger eel nigiri, and a soy sauce ice cream to finish.
Omotesando offers the full spread of Tokyo shopping, big luxury flagships on the main avenue and smaller Japanese labels tucked into the side streets. Off Aoyama-dori, visit Visvim, Needles, and Engineered Garments. Japanese craft, elevated basics, heritage worn lightly.
In the late afternoon, head to Ikejiri-Ohashi for a kissaten reset at DRIP. From the street it reads modern: concrete, low light, vinyl playing. But the bones are old. A pour-over by the cup, a classic pudding with a cherry on top, and a long dark wood bar where the barista works without hurry. Browse their collection of local magazines like Popeye, Brutus, and photo books from around the world.
For dinner, walk fifteen minutes north to Mishuku for the marquee meal of the trip. TEBA (reservation only) is a six-seat counter specializing in Kagoshima fare, specifically fried chicken. The birds are flown in weekly, marinated in a soy-based recipe and dropped to order. Wings, boneless thigh, cartilage, and gizzard, fried to perfection. Don’t skip the house curry rice.
After dinner, walk to Sangenjaya for one last loop. The neighborhood holds onto older Tokyo: paper lanterns glowing in narrow alleys lined with izakayas, salarymen finishing their second beer at a counter, yakitori smoke for ambience. End the night here, then catch the last train back to the hotel.
Destinations Wishlist
Day One
Aman Tokyo. The Otemachi Tower, 1-5-6 Otemachi, Chiyoda-ku. Closest station: Otemachi, Marunouchi/Tozai/Chiyoda/Hanzomon/Mita lines. Aman’s only Japan property; afternoon tea in the Garden Lounge.
Kappabashi-dougu Street. Matsugaya, Taito-ku. Closest station: Tawaramachi, Ginza line. Most shops 9 to 5; many close Sundays.
Asakusa Underground Arcade. Beneath Asakusa Station, Taito-ku. Closest station: Asakusa, Ginza line. Look for the half-curtain counter from Perfect Days.
Five Star Camera. Nishi-Shinjuku, Shinjuku-ku. Closest station: Shinjuku, west exit. Small boutique with film cameras and Y2K digicams behind glass, plus bins worth digging through.
Used Camera BOX. Nishi-Shinjuku, Shinjuku-ku. Closest station: Shinjuku, west exit. A minute’s walk from Five Star; another dense room of vintage bodies and lucky finds.
Tanbo Yoyogi Main Store. Yoyogi, Shibuya-ku. Closest station: Yoyogi, JR Yamanote/Sobu and Oedo lines. Rice cooked to order in donabe, seasonal small plates.
Day Two
Tas Yard. Sendagaya, Shibuya-ku. Closest station: Kita-Sando, Fukutoshin line. Thick-cut French toast and coffee jelly; arrive early on weekends.
Meiji Jingu. 1-1 Yoyogi-Kamizonocho, Shibuya-ku. Closest stations: Harajuku (JR Yamanote), Meiji-jingumae or Kita-Sando (Tokyo Metro). Walk on the side of the path; the center is for the kami.
Omotesando flagships. Minami-Aoyama, Minato-ku. Closest station: Omotesando, Ginza/Hanzomon/Chiyoda lines. Visvim F.I.L., Needles, and Engineered Garments within walking distance.
Mawashi Sushi Katsu. Seibu Shibuya, food floor. Udagawacho, Shibuya-ku. Closest station: Shibuya. Walk in.
DRIP. Ikejiri, Setagaya-ku. Closest station: Ikejiri-Ohashi, Den-en-toshi line. Order the pudding and the pour-over.
TEBA. Mishuku, Setagaya-ku. Closest station: Ikejiri-Ohashi. Introduction-only; reservations required. Doors 17:30 to 23:00.
Sangenjaya alleys. Around Sangenjaya Station, Setagaya-ku. Best after dark, when the lanterns come on.
