Lost in Lisbon: How a Solo Trip Changed the Way I See the World

The Arrival: Gray Skies, Heavy Heart

I didn’t plan on Lisbon. It was a random click on a budget airline site, born out of heartbreak and restlessness. I had just ended a long relationship, and the apartment we once shared felt too full of memories I couldn’t pack away.

Lisbon was far enough. Cheap enough. Mysterious enough.

As the plane descended over the Atlantic and the red rooftops came into view, I had one hope: maybe getting lost would help me find something worth holding onto again.

My First Morning: Cobbled Clarity

I woke to the sound of tram bells and seagulls echoing through narrow stone alleys. Outside my hostel, the morning light painted the walls in honey tones. I bought a pastel de nata from a street cart and sat on a step in Alfama, Lisbon’s oldest district.

The pastry was warm, flaky, perfect. For the first time in weeks, I smiled without forcing it.

Getting Lost on Purpose

Lisbon is a city made for wandering. No straight lines. No sense of hurry. Just stairways that lead to nowhere and tiled buildings that seem to whisper, “Slow down. Look around.”

I walked without a map, letting instinct pull me through shadowed alleyways and sun-drenched plazas. I sipped coffee at outdoor cafés where locals argued in passionate Portuguese. I listened to Fado music one evening—melancholy melodies about longing and fate—and understood every word, even though I didn’t speak the language.

That was Lisbon’s magic. It didn’t require translation. It just required presence.

The Rooftop Dinner That Healed Me

On my third night, I joined a group dinner hosted by a local chef named Joana. Twelve strangers from ten countries gathered on her terrace. As the sun dipped behind the hills, she served fresh grilled sardines, vinho verde, and stories of her grandmother’s recipes.

Next to me sat an older couple from Melbourne, a travel photographer from Chile, and a solo backpacker named Mia from Sweden. We laughed, we shared travel fails, and at one point, we all toasted to the beauty of being exactly where we were—unrooted, open, alive.

I didn’t feel alone. I felt part of something infinite.

The Day Trip to Sintra

Everyone told me not to miss Sintra, the fairytale town just 40 minutes from Lisbon. I took the early train and stepped into another world—lush gardens, candy-colored palaces, fog-laced forests.

I hiked to the Moorish Castle and stood on the ramparts, wind in my face, the Atlantic stretching into mist. Below, the town sparkled like something out of a storybook.

Sintra reminded me that beauty can be overwhelming. That solitude can be sacred. That even ruins hold elegance.

A Chance Encounter

One afternoon, I took Tram 28 up the hills, my camera slung across my shoulder. The tram jolted to a stop, and I tumbled into the lap of a local artist named Paulo. We both laughed. He spoke English. I didn’t fall in love with him, but I did fall in love with the way he described Lisbon:

“This city… she’s like an old record player. Sometimes scratchy, but always playing the song you didn’t know you needed.”

We spent the afternoon sketching people in Praça do Comércio and sipping espresso by the water. I still carry one of his drawings in my journal.

What I Learned From a City That Doesn’t Rush

Lisbon taught me how to breathe again.

It taught me that healing isn’t loud or fast. It’s found in the slow stirring of a spoon in coffee, in the way sunlight hits a wall of blue tiles, in the patience of trams that always seem late but arrive exactly when they’re meant to.

It reminded me that life isn’t linear, and neither is travel. The best paths twist and curve. The best stories meander.

Going Home Different

I spent two weeks in Lisbon. I left with a full heart, a camera roll of sunlit staircases and orange rooftops, and the quiet confidence that I could face the next chapter—whatever it was.

I didn’t find all the answers. But I found me, and that was more than enough.

If You Go to Lisbon

Must-See Spots:

Alfama – Get lost in the oldest part of the city

Miradouro da Senhora do Monte – The best sunset view

LX Factory – A trendy creative space for food, books, and art

Belém Tower – A historic fort with stunning riverside views

Sintra – Day trip for palaces, gardens, and a touch of magic

Eat:

Time Out Market – Gourmet heaven under one roof

Cervejaria Ramiro – Legendary seafood

Stay:

Boutique hotels in Bairro Alto or Principe

Budget-friendly hostels like Home Lisbon Hostel with family-style dinners

Final Thoughts

Lisbon wasn’t the city I wanted. It was the city I didn’t know I needed.

If you’re tired, heartbroken, lost, or just looking for something you can’t name—go. Walk the hills. Eat the pastries. Watch the light change.

And maybe, just maybe, you'll find a version of yourself waiting at the top of a cobbled staircase, smiling in the sun.

About the Author

Wanderlust runs deep in Evanthia Giannou's soul, and Lisbon stole a piece of their heart. With a curious spirit and a love for storytelling, Evanthia Giannou explores cities not just through sights, but through flavors, people, and quiet moments off the beaten path. When not chasing sunsets in Portugal or sipping espresso in a hidden café, they’re sharing travel stories to inspire others to find magic in every journey.