My stomach is grumbling – Pocky is all that’s tiding me over until lunch today. We’re headed to Osaka’s famed food market, Kuromon, and I plan to apply the same logic to my belly as my luggage: arrive half-empty and fill it at the destination. Right now, I’m either hangry or this metro station is unusually confusing, but our Intrepid local leader Yuki knows exactly the right elevators to get us out quicker.

Thankfully our group doesn’t draw attention as a bigger horde might, and it’s easier to weave through the maze. There are 12 of us, including solo travellers from England and the Philippines; a pair of cousins from Australia; two sisters from Switzerland; couples from the US and Ireland; Broadsheet photographer Yusuke; and myself.

Yuki guides us out of the station towards the hotel Intrepid has arranged. We lug our bags past Sankaku (Triangle) Park, a popular meeting spot in shopping district Amerika-mura. Amemura, as it’s known to locals, is a fashion- and culture-generating neighbourhood that generally elicits the words “trendy” and “youths” online. Named after a flush of Western fashion stores opened in the ’60s, it still teems with fashion boutiques curating distinct spins on American vintage. And it’s where we’re calling home for the final night of Intrepid’s eight-day Japan Highlights tour.

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Kuromon Market

Yuki checks us in to our hotel and, as if she can hear my stomach grumble, takes us straight to lunch. We walk around Kuromon Market, which looks a bit like a street-food arcade. The air inside is smoky and smells of hot grills and fresh seafood. Yuki has ordered ahead for the group and there’s already a tower of okonomiyaki awaiting in Hananoki, a 30-year-old store specialising in the savoury pancakes. She knows exactly what to get from the menu: a couple with squid and octopus, and some with scallops, octopus and cheese.

Okonomiyaki flavours vary between regions and stores play fast and loose with the recipes; okonomi means “whatever you like” and yaki is “grilled”. Everyone in the group takes a bite, followed by satisfied groans and shared wide-eyed glances. The next stall sells cups of fresh Japanese sweet potato crisps that a curious groupmate, one of the two Swiss sisters, shouts for everyone. After I wipe potato crumbs off my shirt, Yuki gives us our return time and I break away to begin my mission: kuidaore.

Kuidaore is the local word meaning to “eat yourself broke” or “eat ‘til you drop”. I begin with two palm-sized fillets of glistening skewered unagi (eel) that are so soft I slurp them right off the stick. I move on to another stall: three decadent slabs of salty and fatty A5-grade Kobe beef. Then, a plate of oshizushi (pressed sushi) with mackerel. And my last stop is an old mochi store using the same wooden displays since it opened more than 70 years ago. I arrived at dessert sooner than expected, and I’m yet to declare kuidaore. Good thing I still have an afternoon of exploring to do.

Dotonbori

After the market, Yuki guides us to Dotonbori to experience the famed main drag. It’s one of the top attractions in Osaka, so Yuki brings us to check it out when it’s a little more manageable. “They call it the street that never sleeps. If you think this is busy, wait ‘til you see it at night!”

There’s a circus-like atmosphere here, with metres-tall mascots hanging from restaurant facades. There are neon lights, bars everywhere, and a rainbow-clad band floating down a canal. “Maybe I’m still hungry,” I think as I lock eyes with a noodle-wielding dragon. I’m starting to understand Chihiro’s parents surrendering to the food in Spirited Away. Our walking tour ends at the famous Glico Running Man sign where our group commemorates our newfound friendships with a photo – copying his jogging stance, of course.

We’ve got a few hours to spare, and I want to explore a different kuidaore. Kuidaore Taro is a famous Osakan clown character, dressed in a striped outfit and cone hat, whose likeness I keep seeing around Osaka in an involuntary game of Where’s Wally?

Along with being considered a food capital, Osaka is renowned for its comedy acts and bars – Taro embodies the city’s love for both. I get last-minute tickets to the daily show at a theatre called Namba Grand Kagetsu. There are a few shows a day with performances by a revolving comedy collection ranging from local acts to national legends. “Most people in Japan would know this man,” says Yusuke when Bunchin Katsura walks on stage. “We’re lucky to see him.”

At the gift shop, I finally trace the name and story behind the ever-present Taro. He’s a mechanical statue once associated with a restaurant in the Nakaza Kuidaore Building. Though the restaurant closed in 2008, the original statue still stands proudly while his character has become a mascot for the area.

On our way back to the hotel, we drop by doll-themed otaku bar (otaku is a term for “geeks” with niche obsessions) Element L, visit renowned hip-hop store Hifumiya, and pop our heads into otaku space Milulari, where a DJ is breaking out into a trumpet solo.

Osaka after dark

In the evening, we get together for our final outing as a group. Some, like myself, are headed home tomorrow, while others continue their travels in Japan.

We walk a minute to an izakaya specialising in kushikatsu, deep-fried skewers, including crumbed prawns, lotus root and chicken. We have the whole top floor to ourselves, and after eight sticks and a couple highballs, spirits are high. After our meal, Yuki gathers us all on the balcony to express her appreciation for our group, prompting everybody to say a few words. There’s a unanimous shared sentiment of admiration for the bond (and inside jokes) formed in just eight days, and a promise to keep in touch.

But we’re not ready to say goodbye. Instead, we head to a nearby venue the American couple saw on Tiktok – a retro gaming bar called Space Station. The bar is lined with Nintendo 64 game cartridges, and I load up Mario Kart 64 and challenge Yuki. Though she’s spent this tour at the front guiding the group, she finds herself at the end of the pack in the game. After a few races (and laps driving backwards), we share our final goodbyes.

Since it’s my last night, Yusuke and I decide to visit the fabled Misono Building, a choose-your-own-adventure labyrinth of bars. Up a large spiral staircase, there are two floors each with dozens of small, themed venues. It’s a bit intimidating to choose, so follow your ears and park at whichever plays your kind of music. At Bar 1492, a patron brings in a box of caneles to share with everyone. As I bite into it, I realise that Osaka might be ruining me with food.

When Bar 1492 closes around 3am, owner Eri Takii takes everyone out for a late-night feed at Obanzai Sakamachi Haikara. She orders a big bowl of udon, mapo tofu and a plate of sashimi – including a serve of raw chicken sashimi that she assures us is safe to eat here. It’s 4am and I’m not in a state to argue, but I watch everyone else eat it first in case it’s a tourist prank.

As we say goodbye, Takii rallies everyone into a circle. “Otewoawasete,” she says, instructing us to put our hands together for ippon-jime, a synchronous clapping ritual that marks the end of a gathering. I’m a few claps behind, and I’m wondering how I’ve ended up in an alley in Osaka at dawn.

In seven days, I’ve trekked from Tokyo into the countryside, through Kyoto’s lantern-lit alleys, and into a food coma in Osaka. The Japan Highlights tour is fast, but I haven’t felt rushed. And I’ve seen more of Japan than I thought possible in a week. As I waddle away from my new friends, I wrap my hands around my stomach. I think I feel it. Not the chicken sashimi, but a perfectly full belly – this must be kuidaore.

This article is produced by Broadsheet in partnership with Intrepid Travel. Intrepid’s Japan Highlights tour is a fully guided eight-day trip that includes all transport and accommodation. Starting in Tokyo and finishing in Osaka, it takes in city and country – including a farmstay and some gentle hikes. Find out more here.