The Crew Assembles
When the five of us landed at Taoyuan on a Thursday afternoon—me, Ben, Mia, Noah, and Sarah—we had a loose itinerary written on the back of a napkin and absolutely no idea what we were doing. I'd been to Taiwan twice before, Noah had read a food blog, and the rest were operating on pure faith and my promise that "the street food alone justifies the flight."
We dumped our bags at a guesthouse in Daan and decided to start the next morning with breakfast. Not hotel breakfast. Not even a "nice" restaurant. We wanted the real thing.
Pedalling Into the City's Actual Life
At 6:47 a.m., bleary and jet-lagged, we rolled up to meet our guide for the Best E-bike Cycling Tour in Taipei - Includes Local Food & Drinks Best E-bike Cycling Tour in Taipei - Includes Local Food & Drinks. Mia had booked this days earlier—a five-hour loop that would take us through Taipei before the city woke up properly.
Our guide, Wei, arrived on a bright red e-bike with the energy of someone who'd already had three coffees. "Most tourists see Taipei from a bus window," he said, handing each of us a helmet. "Today you see it like a person who lives here."
He wasn't exaggerating. We pedalled through residential alleys where vendors were still setting up their stalls, past temples with smoke curling from incense pots, and into a breakfast market that smelled like a fever dream of soy sauce, sesame oil, and youtiao (fried dough). Wei ordered for everyone—a round of dumplings, scallion pancakes, salty soy milk so rich it tasted like umami's grandfather.
Ben, who'd been quiet all morning, actually closed his eyes while eating. "I need to live here," he announced to no one in particular.
The e-bikes took the terror out of Taipei's traffic. We glided up to Taipei 101, wheeled through the riverside parks, and stopped at a local tea vendor who insisted on explaining the provenance of her oolong like it was a Burgundy vintage. By the time we reached the end, thighs burning and faces flushed, we'd covered fifteen kilometres, absorbed about four hours of urban navigation, and understood exactly why people get evangelical about this city.
Inside the Dumpling
That evening, we showed up at a modest apartment building in Taipei for the Xiao Long Bao, Pork thick soup, Bubble milk tea. Taiwan Traditional Light Meals Experience-B (Taipei Cooking Class) Xiao Long Bao, Pork thick soup, Bubble milk tea. Taiwan Traditional Light Meals Experience-B (Taipei Cooking Class). Noah had been talking about this for weeks. He's the kind of person who watches dumpling tutorials at midnight.
Our teacher, Hsiu, was a woman in her sixties who'd been making xiaolongbao since she was eight years old. Her kitchen was small, warm, and smelled like pork stock simmering for what she said was "the correct time." The correct time, it turned out, was six hours minimum.
"You see?" She held up a dumpling wrapper, translucent and perfect. "The skin, it tells you everything. Too thick, you taste only dough. Too thin, it breaks. This—this is the conversation between hand and dough."
We spent two and a half hours folding, twisting, and failing spectacularly. Sarah's dumplings looked like they'd survived a minor earthquake. Mine were passable—Hsiu was kind. Noah's were almost acceptable by about the twentieth attempt. But Mia somehow produced three that looked commercially perfect. Hsiu laughed and refused to let Mia help further. "You make me look bad," she said, grinning.
We then learned to make the pork thick soup—a silky, deeply savoury broth that Hsiu revealed contained pork, mushrooms, and patience. When we steamed our dumplings and finally ate them, pulling apart those wrinkled, treasure-filled purses, every single one of us understood why people write poems about xiaolongbao. The broth inside was a small heat-packet of salt and richness and home.
Bubble tea came last—simpler than we expected, more technical than we'd guessed—and by the time we left, we'd collectively decided that Hsiu was now a personal friend and we'd be naming our theoretical future children after her.
The Old City Never Left
The next morning, Sarah led us on the 2-Hour Private Dadaocheng Walking Tour 2-Hour Private Dadaocheng Walking Tour. She'd been drawn to this neighbourhood from a history book about 19th-century Taipei, and honestly, so had I.
Dadaocheng is what happens when you stop trying to make a city look modern and let the past sit alongside the present like old friends at a bar. Our guide, a woman named Lin, pointed out the heritage shopfronts that still sell tea, textiles, and traditional medicines in the same way merchants did 150 years ago. The streets are narrow enough that you can practically shake hands across them.
We stopped in a tea merchant's shop where the owner—who Lin knew personally—let us smell the difference between four types of oolong. Sarah bought a small packet of high-mountain tea that cost more than I'm comfortable admitting to on company expense reports. Ben bought vintage silk scarves he has no practical use for.
Line insisted on taking us into a noodle shop that wasn't a tourist attraction, just a place where people ate. The owner didn't speak English and hadn't updated the decor since 1987, which made it immediately perfect. The noodles were hand-pulled, the broth was dark and complex, and we sat elbow-to-elbow with construction workers and retirees who ignored us entirely. This felt like actual Taipei—not the postcard version.
When You Give Up Planning
By day four, we'd fallen into a rhythm: early breakfasts, long conversations about which dumpling had the best wrapper consistency, arguments about the correct temperature for oolong. And then Ben got food poisoning—not seriously, just enough to demand a day on a couch—and we had to entirely restructure.
Over congratulatory beers, we made an executive decision: instead of scrambling around Taipei separately, we'd book the 5-Day Round Taiwan Charter Car Tour 5-Day Round Taiwan Charter Car Tour for the final stretch. Our original plan had been to bounce around on trains, but honestly, we were tired. We wanted a driver, a vehicle, and the simple freedom to stop wherever something caught our eye.
Our charter driver, a quiet man named Ming, arrived in a pristine seven-seater van. He'd been doing this for twelve years and had the particular gift of knowing exactly when to talk and when to let you sit in silence watching the landscape change.
We drove south toward Taichung, stopped in Changhua for oyster omelettes that required a debate about whether the egg or the oyster was the hero, swung past some temples nobody on the internet had told us about, and ended up in a small town where Mia spotted a night market and basically lost her mind.
On the final morning, we were somewhere near the eastern coast, watching fishermen work in the kind of light that makes you understand why painters move to Asia. Nobody was on their phone. Everyone was quiet in the way that means you're actually paying attention to being alive.
The Thing About Traveling With People
When you spend a week with four other people eating, cycling, cooking, and driving through an island that refuses to perform for tourists, something happens. You stop being travelers and become something closer to a small temporary family.
I learned that Noah cries when food is this good. Mia navigates using only her sense of smell and geographical intuition. Sarah reads plaques and takes notes. Ben eats literally everything and offers non-stop commentary like a sports announcer. And somewhere between the xiaolongbao and the oyster omelettes and the fifth cup of excellent tea, we stopped being Global Hobo crew members on assignment and just became five people in love with this strange, precise, kind island.
Taiwan didn't change us. But it definitely made us pay attention.
