Do You Remember Your First Time?

Woman looking at the panoramic view of Lisbon's traditional red roofs and river on a sunny day
That moment when the city wraps you in a warm, sunlit hug.

I still remember that day in February 2019

I first stepped into the Baixa-Chiado neighborhood.

My startup colleague and I had just flown in from a freezing, snow-covered city. Almost instantly, Lisbon wrapped us in a warm, sunlit hug. I remember the trees were still bare, and locals were bundled up in puffer jackets and zipped-up sweaters. But when you come from -20°C, a local +20°C feels like pure bliss.

The reaction was instant: off with the heavy winter layers. Just a light dress, comfortable sneakers, and a crossbody bag with the bare essentials.

Walking down a traditional cobblestone street with tram tracks in the Chiado neighborhood, Lisbon
Sometimes the best way to explore is to put the map away and just follow the streets.

The smell of fresh, buttery pastries filling the air, the iconic yellow trams rattling by, the multilingual hum of the crowds… if you catch the right vibe, you blend into this city immediately.

Lisbon’s streets are 3D, but Google Maps still thinks the world is flat.

I clearly remember trying to find a specific spot on Google Maps that day. It was a disaster.

The app was completely confused. It couldn’t process the multi-level streets, the sudden hidden staircases, and the winding alleys. It kept telling me to walk straight through buildings.

Eventually, I gave up and had to ask the locals for directions. That was the exact moment I realized something important: Lisbon is a city of people, not technologies.

Locals happily pointed the way. We didn’t always understand each other perfectly, but we were completely fine with getting lost. It was a perfect match.

A lot of time has passed since that February day, and a lot has changed….Today, if you ask a barista if they have “Apple Pay,” there’s no doubt they’ll pull out the card terminal rather than serving you an apple pie.

But despite the modern upgrades, the core magic remains.

Today, I have returned to Lisbon to actually live here. I am ready to uncover its new sides and explore its different facets constantly. To rediscover it every single day.

So, tell me… Do you remember your first time in Lisbon? What was it like? Did you get lost on the stairs too? > Drop a comment below — I read every single one.

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