Biking Adventures in Osaka

On slow, relaxed days spent biking with friends, it’s all about the journey, not the destination.

Most summers for the past few years, I’ve spent long days biking in leisurely loops around Osaka, Japan. I go to visit local buddies, but also to eat, walk, drink, and hang around their beautiful city, an intricately layered urban grid that’s still easygoing and open, with its plethora of green spaces set against skyscrapers.

Somewhere along the way, we started getting around by bike. This routine of cycling from neighborhood to neighborhood in the heat was born. Coming from Houston, I always thought the idea of a bikeable city was fantastical. However, I have since realized that cycling allows me to truly experience a place. It is a small, private pleasure, and unless I’ve rolled a bike around a city—pausing at intersections and fanning myself as I heel the kickstand and rest beside buildings—I seldom feel grounded.

Osaka is massive, composed of 24 wards. Two of its prominent city centers are Umeda, the northern district where tourists go to shop and be seen, and Namba in the south, known for its nightlife and bright lights. Despite the city’s size, it’s still approachable, allowing you to slide through multiple districts in a single trip. If I feel brave (a rare thing), I might trek out on my own, but mostly, I relish the chance to ride with friends, wheeling from bar to bar.

One morning a few Augusts ago, my buddy R. and I set out on what we’d planned to be a casual daytime ride along a familiar route. It was the week of Obon, a major Japanese holiday during which folks honor their ancestors, so there weren’t too many cars on the road throughout the business district. As I trailed R. on his bike, he used hand signals to direct me through alleys and across bridges. Occasionally, we found ourselves beside a car; I’d nod at the passengers, and they’d give us a shrug or a smirk or a wave.

As the morning wore on and transformed into a sweaty afternoon, R. and I wheeled from one neighborhood park to another, alternating between a lighter pace and occasional bursts of speed. We rested between a pair of shrines before pedaling uphill to a tiny market in the center of the old town, where we paused in front of a woman selling okonomiyaki, a popular savory pancake drizzled with Japanese-style mayonnaise. A few miles later, we enjoyed our meal hunched over our bikes, feeling the midday humidity and lamenting that we hadn’t bought extra pancakes.

Experience the Most Beautiful Cities for Biking

I had a big trip the next day—I was taking the bullet train to Tokyo, where I would catch the first leg of a long flight home—and even though it felt like pushing my luck to stay out, R. and I met up with another buddy, K. Several hours later, we made our way out of a gay bar, hopped on our bikes, and started a slow glide around Doyama, the center of the city’s queer nightlife.

The streets had started to fill. The three of us dipped between buildings and eventually settled in a single-file line. We passed gaggles of businessmen walking home from after-work beers and couples strolling hand in hand—and even a few solo bikers, who joined our trajectory for a time before turning off and disappearing back into the city.

“It had been an eventful evening,” R. said—slurred, really—that Osaka was a city where anything that could ever happen to a place had already happened. If you tried hard enough, you could cup the whole town in your hands.

These were streets I’d spent months wandering, feeling a gravity pull me through them. Now, with the knowledge that I was about to leave, the ride felt like an end. However, as long as we stayed on the bikes, maybe the present could last a little bit longer.

We kept going until well after midnight, meandering from one pocket of the city to another, before finally parking our bikes in front of a fruit-juice vendor, who handed us an oversized cup we all shared. It had indeed been an eventful evening, and R. said—slurred, really—that Osaka was a city where anything that could ever happen to a place had already happened. If you tried hard enough, you could cup the whole town in your hands.

K. then told him that was nice, but to please shut up. R. squinted, deeply, and cupped both of K.’s hands. It was maybe four in the morning, and we were the only ones on the road, but this place felt very crowded, very lived-in. So K. followed suit with his palms, and I did, too.

We biked two more laps on our usual circuit and stopped at the edge of a bridge. The morning traffic wasn’t much more than a handful of taxis. The three of us leaned over our bikes, panting, taking it all in. Then K. asked me if I had caught my breath. I told him we were good, and we probably had time for another lap.

A version of this story first appeared in the August 2021 issue of iBestTravel under the headline Full Circle.