The Tuk-Tuk That Swallowed My Skepticism
I arrived in Lisbon at 11 p.m. on a Tuesday with the sort of hangover that makes you question your life choices and the kind of cynicism that comes from five years of dodging tourist-infested paella joints across Europe. My plan was simple: stay in Príncipe Real, find the grittiest bar I could locate, and avoid anything that smelled like Instagram.
Then my colleague Mia texted. "Do the tuk-tuk tour but at sunset, not dawn." Mia has never steered me wrong, so I booked the All City Premium Private Guided Tour by Tuk-Tuk in Lisbon All City Premium Private Guided Tour by Tuk-Tuk in Lisbon for the following afternoon, figuring I'd get the neighbourhoods down before the nocturnal crawl.
What I didn't expect was to fall half in love with my driver, a woman named Joana who'd been steering tourists through Lisbon's hills for twelve years and had the kind of deadpan humour that suggested she'd seen every cliché and learned to weaponise her indifference. We started at Praça do Comércio—yes, yes, the postcard square—but Joana didn't linger. Instead, she threaded us through Mouraria's narrow lanes where laundry hung like bunting and old men played cards in doorways. The tuk-tuk wheezed up impossible gradients, squeezed through alleys that looked too narrow to survive, and emerged in Alfama just as the light turned golden and vicious.
"The tourists come here at 10 a.m.," Joana said, gesturing at the empty streets. "They take their photos. They leave. They never come back."
Then we climbed to Graça—Joana's neighbourhood, she said—where the hilltop views sprawled across the terracottas and the Tagus cut through everything like a scar. A group of old women were gossiping on a bench. A cat, orange and enormous, owned the entire street. This was the Lisbon I'd come for: the one that doesn't market itself.
We finished in Chiado as the sun actually set, threading past the literary bars where Pessoa used to haunt himself into existence. Joana dropped me with a recommendation: "Forget the rooftop bars. Go to Café Tati in Graça. Order a Super Bock. Talk to no one."
The River Wanted Blood
Two days later I was on a coach heading north, restless and caffeinated, because someone at Global Hobo HQ had suggested I couldn't call myself a dirtbag without doing something moderately terrifying.
Melgaço sits at the edge of the Minho valley where Portugal meets Spain and the landscape turns suddenly severe. I was there because Ben—our most reliably chaotic team member—had done the Private Rafting Experience in Melgaço Private Rafting Experience in Melgaço and kept sending me photographs of whitewater that looked actively hostile.
Our guide was a man named Rui who'd clearly spent his entire life in a river and had the kind of calmness that comes from having survived things. He strapped me into a life jacket that smelled like mildew and other people's terror, pointed to an inflatable boat, and said: "Three hours. You will be wet. You might be scared. This is normal."
The Minho in late September is not fucking around. It's the tail end of the summer discharge, all vindication and force, and within fifteen minutes of paddling I understood that this wasn't an extreme-sport Instagram moment—this was actual risk, the kind that makes your nervous system scream at you to get out of the water and do something sensible like write poetry or become an accountant.
Rui navigated us through a canyon system that felt genuinely ancient, where the water turned from grey to proper white and the rocks narrowed until I couldn't see sky. My arms burned. My shoulders threatened mutiny. At one point I looked at the couple next to me in the raft—American honeymooners, utterly terrified—and we locked eyes with the shared understanding that we might die together in the middle of nowhere and that this was somehow hilarious.
We didn't die. We got soaked. Rui pulled us out at a beach bar where a woman served us something called a Francesinha that was essentially a sandwich attempting suicide, and suddenly the fear rewired itself into pure elation. We'd survived. The river hadn't killed us. We ordered another round.
The Painter and His Rooftops
Back in Porto three days later, I needed something meditative to balance the adrenaline. Mia had mentioned a painter. Hugo do Lago operated out of a tucked-away studio gallery in the Sé neighbourhood, and when I showed up—hungover, sceptical, ready to hate the whole enterprise—something shifted.
The Create Watercolour With Hugo do Lago in Porto Create Watercolour With Hugo do Lago in Porto session was supposed to be two hours of painting the city's dramatic rooflines. What it actually was: watching an artist argue with his city through pigment and water, and slowly realising I was arguing too.
Hugo didn't teach technique first. He made coffee. He showed us photographs of Porto's underbelly—the parts tourists don't film. He talked about how the city's geometry was a conversation between decay and beauty, how you couldn't paint the rooflines without understanding the weight underneath them.
Then he handed us brushes.
I'm not an artist. I can barely draw a line that doesn't look like a seizure. But something about Porto—the light, the river, the sense that this city was watching you back—made the watercolour less about accuracy and more about honesty. My painting looked like chaos. It looked like what I felt. Hugo looked at it and said: "This is good. It is wrong, but it is good."
We drank wine in his studio as the sun dropped, and he talked about why he stayed in Porto instead of moving somewhere more fashionable, more profitable. "Because," he said, "if I left, the city would forget how to argue with itself."
The Long Game
My flight out was from Faro, south, the tourist-trap capital. I'd meant to spend the day finding abandoned churches and dingy fado bars, but exhaustion—the good kind—had set in. Instead, I booked the Faro Airport Private Transfer to Carvoeiro Faro Airport Private Transfer to Carvoeiro to at least see the Algarve without the faff of hunting for transport.
The drive took ninety minutes. My driver, Carlos, was seventies, quiet, had clearly seen the Algarve transform from something real into something packaged and resold. We didn't talk much. Sometimes you don't need to. Sometimes sitting in an air-conditioned car watching a landscape roll past is exactly the right kind of meditation.
Carvoeiro looked postcard-perfect in the afternoon light. I walked to the beach, sat on a bench, and thought about Joana and the tuk-tuk, about Rui pulling us through the whitewater canyon, about Hugo arguing with rooftops. This is what the night-time travels teach you: Portugal isn't better when it's dark. It's just more honest.
Sometimes the best adventures aren't the ones that look good in photographs. Sometimes they're the ones that stick under your skin, make you argue with cities, make you understand that the whole point of travel is to find the places that don't want to be found.
I'm already planning my return. Joana says the winter Tagus is something else entirely.
