To Lisbon, With Love
A Journey of Overcoming Fear, Starting Over, and Realizing One Pair of Shoes Is Never Enough
By Anna L. Williams
It was somewhere over the Atlantic Ocean, in the darkest part of the night, when I realized my mother had somehow stowed away in my brain. Not literally, of course—she hates flying, says it gives her "the bends," which isn’t even the right terminology—but there she was, firmly ensconced in my psyche, whispering about the many dangers of traveling abroad. But I had resolved to make this trip to Lisbon, Portugal, the first international trip of my adult life, as a statement: to her, to myself, and to my new employers in publishing who seemed baffled by my insistence on a pre-start date vacation. I figured, if I’m going to start at the bottom rung again at 42, I might as well do it with a tan.
And that was when I realized: I’d only packed one pair of shoes. One pair. For three days. In a foreign country. And not even sensible ones. But as my therapy-addled mind has recently learned to say: “There’s no such thing as failure, only feedback.” Lisbon, here I come.
My three-day escapade in Lisbon would be a leap of faith, a cocktail of fear, curiosity, and a splash of adventure. Lisbon, the city of seven hills, Fado music, and custard tarts, was to be my first foray into international travel, a trip my younger self had only dreamt about between the pages of glossy magazines. Armed with a publishing career reboot and a determination to silence my mother's travel-induced anxieties, I set out to explore Lisbon’s cobbled streets, iconic yellow trams, and gastronomic delights—all while navigating the pitfalls of my singular, impractical footwear choice.
Day 1: A City Unfolds Beneath My Feet (and My Feet Protest)
I arrived at the Memmo Alfama, a boutique hotel tucked away in the winding alleys of Lisbon’s oldest district, Alfama. With its terracotta rooftops and maze-like streets, Alfama felt like stepping into a postcard. The hotel was charmingly modern, with a rooftop terrace that offered panoramic views of the Tagus River, but my feet were already regretting the leather sandals I had unwisely chosen as my sole companions.
After freshening up (read: scrubbing off 14 hours of plane grime and regretting the life choices that led to this single-shoe debacle), I set out to explore. Alfama’s narrow, steep streets quickly tested my resolve. Each cobblestone seemed determined to wage war against my arches, and it dawned on me that perhaps more planning (or perhaps just an ounce of common sense) would have been wise. Nonetheless, I soldiered on, each step a small victory against my mother’s voice in my head.
My first stop was Castelo de São Jorge, a Moorish castle perched high above the city, where I expected to be wowed by history and views of Lisbon sprawling beneath. What I didn't expect was to spend 20 minutes trapped in a pigeon-related standoff, thanks to my open-toe situation. Eventually, I was able to navigate around the avian blockade and made it to the castle's highest point. The view was spectacular, Lisbon laid out like a patchwork quilt of red, orange, and yellow buildings, stitched together with winding alleyways.
After a lunch of bacalhau à brás—Portugal’s signature salt cod dish—I found myself in Terreiro do Paço, a vast plaza by the river. I was struck by the openness of it, the way it seemed to breathe as the wind swept across the water, carrying with it a sense of possibility and, unfortunately, the sharp, blistering reminder of my ill-chosen footwear.
Day 2: Culinary Revelation and Fado Under Stars
The next morning, I decided to tackle my footwear problem head-on. I ventured to Chiado, Lisbon’s fashionable district, to procure a second pair of shoes. However, instead of finding sensible sneakers, I was seduced by a pair of wedge sandals, somehow managing to make my shoe situation both better and worse. Feeling slightly more balanced (in spirit if not in foot support), I continued to explore.
Lisbon’s food scene was a revelation. I found myself at Taberna da Rua das Flores, a small, unassuming restaurant where the food was anything but. The meal began with octopus salad—tender, tangy, with a hint of lemon and garlic that lingered long after the last bite. Then came the star: pork cheek with sweet potato puree. It was rich and flavorful, a dish that felt like a warm hug after a long day. I was so engrossed in the flavors that I nearly forgot about my feet, a small victory in itself.
Nightfall found me in the Bairro Alto neighborhood, famed for its vibrant nightlife. I had been curious about Fado, the melancholic Portuguese music that speaks of love, loss, and longing, and I found myself at a tiny Fado house, where I was swept away by the soulful melodies and the emotion in the singer’s voice. I didn’t understand a word, but I felt every note. Perhaps it was the wine, or the haunting strains of the guitar, but I found myself tearing up. I blamed it on the shoes.
Day 3: Finding Closure Among the Ruins
On my final day, I ventured to the Jerónimos Monastery in Belém, a breathtaking display of Manueline architecture. The monastery, a UNESCO World Heritage site, was a testament to Portugal's Age of Discovery, its grandeur both awe-inspiring and humbling. As I wandered through its cloisters, I thought about my own small discovery journey, my own need for exploration, not just of places, but of self. I had come to Lisbon to prove a point—to my mother, to myself—that I could step outside the boundaries of my comfort zone and thrive.
Later, I made my way to the Pastéis de Belém, home to Lisbon's famous custard tarts. The line was long, but the wait was worth it. I bit into the flaky pastry, and the creamy, sweet custard filling exploded in my mouth. It was a moment of pure joy, the kind of bliss that makes the blisters and the foot pain worth it.
That night, I found myself back at the hotel’s rooftop terrace, a glass of vinho verde in hand, overlooking the city that had tested me, challenged me, and ultimately, welcomed me. The breeze carried the distant sound of Fado, and for a moment, I felt a sense of peace—a quiet victory over my fears.
Yes, I had only brought one pair of shoes. But in those three days, Lisbon had taught me that sometimes, the best journeys are the ones that are a little bit uncomfortable, a little bit unplanned, and a lot bit unforgettable.
And maybe, just maybe, next time, I’ll pack two pairs.
