The Tuk-Tuk Gamble
I arrived in Lisbon on a Tuesday with a hangover I'd inherited from Barcelona and zero plan. The Praça do Comércio was already thick with cruise-ship dregs when I stumbled out of my pension, so I did what I always do: I looked for the thing that absolutely terrified me.
That thing was a three-wheeled vehicle and a stranger named João.
I'd booked the All City Premium Private Guided Tour by Tuk-Tuk in Lisbon All City Premium Private Guided Tour by Tuk-Tuk in Lisbon partly because it seemed ridiculous, partly because four hours of forced conversation would either cure my solitude or finish me off. João picked me up from my hotel in a tuktuk that smelled like cigarettes and pine air freshener, which I later learned is the official scent of Lisbon.
We shot through Mouraria's narrow lanes at what felt like illegal speed. Laundry hung like prayer flags between buildings that looked ready to surrender to gravity. An old man was feeding pigeons from a tin cup. A kid on a scooter nearly took out my knee. "Very authentic," João said with a grin that suggested he knew exactly how close that was.
Alfama was the usual suspects—tourists and tram tracks—but João knew which alleys to duck into, the ones where residents actually lived instead of posing. We climbed to Graça's hilltop viewpoint where the whole city sprawled below like a drunk watercolour painting. Chiado's literary cafés came next, the ones Pessoa probably drank in, though I mercifully missed the hordes by timing it for late afternoon.
For four hours, João talked. About his ex-wife. About why he'd become a tuk-tuk driver after working in banking. About the time he drove a German family whose sat-nav tried to route them through the Tagus. I barely said anything. I just watched the city move past and felt the knot in my chest—the one that comes from travelling alone—start to loosen.
Northern Nights
From Lisbon, I took a night train north because that's what people like me do. We chase the uncomfortable because comfort is predictable.
Melgaço, tucked into the Minho valley near the Spanish border, is the sort of place that doesn't appear in most guidebooks. It's also the sort of place where you can get yourself into the kind of trouble that makes for decent stories later.
I'd booked the Private Rafting Experience in Melgaço Private Rafting Experience in Melgaço on a whim, having never whitewater-rafted before. The logic was: what's the worst that could happen? (Spoiler: you don't want to know.)
My guide, Pedro, collected me at dawn from the village's single café. He was the kind of lean, quiet person who exudes competence without needing to mention it. The Minho River was high from recent rain—"Better for excitement," he said, which I'm now fairly certain was Portuguese for "better for nearly drowning."
Three hours on that river taught me a few things: that my upper body strength is fictional, that cold water is a religion unto itself, and that the moment just before a proper rapid hits is the moment when your brain finally shuts up. No thoughts. Just the river.
We flipped once. It was entirely my fault. I was reaching for a camera shot—the cliffs of the Minho valley, the Spanish side glinting in the morning light—when a wave caught the boat's side and suddenly I was underwater, gasping like a landed fish. Pedro fished me out with the efficiency of someone who'd done this exact thing before. "You okay?" he asked, barely interested.
I was more than okay. I was alive in a way that sitting in a flat drinking coffee couldn't touch.
The Paint-Stained Detour
By the time I reached Porto, I was craving something quiet. Something indoors, ideally with minimal risk of drowning.
I'd stumbled onto a listing for Create Watercolour With Hugo do Lago in Porto Create Watercolour With Hugo do Lago in Porto at 3 a.m. in a hostel common room whilst half-drunk on cheap wine, and I'd booked it because my brain was clearly still misfiring from the river experience.
Hugo's studio was tucked away in the Sé neighbourhood, exactly the kind of place you'd find if you were lost. Exactly the kind of place you'd miss if you were following a map.
Two hours. That's how long I sat with Hugo, a 60-something painter with stained fingers and the patience of someone who genuinely didn't mind that his student was producing something that looked like a drunk giraffe had attacked the paper.
We painted Porto's rooflines. The Douro River. The tiles and terracotta and that particular light you get when you're standing on the right side of a European city at the right time of day. I wasn't good. I was genuinely, impressively bad. But for two hours, I didn't think about home or my job or why solo travel felt like self-flagellation with better scenery.
Hugo drank coffee. Occasionally he'd lean over and make a correction so subtle I almost didn't notice—a darker wash, a sharper line. "You see?" he'd say. "Sometimes less is more." He wasn't talking about watercolours.
South, Brief
Madeira felt like a cheat—too easy, too gorgeous, too far from the gritty truth I'd been chasing. But I went anyway.
I booked the Level 1 - Canyoning For All - Beginner in Funchal Level 1 - Canyoning For All - Beginner | Funchal because apparently one near-death experience per trip is my baseline, and dry land felt suspicious.
The guide, André, picked me up from central Funchal and drove us into a forest so green it looked photoshopped. "Have you done this before?" he asked.
"Rafting once," I said. "Badly."
He laughed. "Then you're ready."
The canyoning was technical without being impossible—abseiling down a canyon face, jumping into pools of water so clear you could see the rocks beneath, walking through tunnels carved by water over centuries. It was the kind of activity that sounds terrifying in description and feels transcendent when you're actually doing it.
By the final pool, I was thinking less about the activity and more about what I'd figured out so far: that solo travel isn't actually about being alone. It's about being available for something larger than your own narrative. A river. A guide. A stranger in a tuk-tuk.
The Practical Bit
On my way south to the Algarve for the flight home, I booked the Faro Airport Private Transfer to Carvoeiro Faro Airport Private Transfer to Carvoeiro because I'd learned that if you can afford to skip the bus-queue shuffle, you should, especially after a month of living rough.
The driver—taciturn, efficient, knew every pothole—drove me along the coast where the cliffs were the colour of rust and the sea was still doing its thing below.
Portugal had done its thing, too. Not because I'd ticked boxes or followed an itinerary. Because I'd said yes to the stupid, the scary, the quiet, and the ordinary. Because a night train is sometimes the only honest transportation. Because a tuk-tuk ride can teach you more about loneliness than a year of self-help books.
I'd arrived looking for clichés and left with calluses, a watercolour that looked like a drunk giraffe, and a soaking-wet photograph of the Minho valley.
Not bad for a month of saying yes to trouble.
