Travel Without Filters: Escaping the Algorithm to Rediscover the World
- Jun 21
- 6 min read
There's a version of travel planning that feels very efficient. You open a browser, ask an AI assistant for an itinerary, cross-reference it with Instagram recommendations, check TripAdvisor, scan a few Facebook groups, and end up with a color-coded schedule that accounts for nearly every hour of your trip. I've done versions of this. It has its uses. But these tools are not neutral. Search engines favor large platforms and paid listings. Social media amplifies destinations with high engagement, not necessarily high value. And because they track what you've searched before, they tend to show you more of what you already know, quietly narrowing your options without you noticing. Some of the best moments I've had as a traveler have come from the spaces between the plan, and from the decades I spent traveling before any of these tools existed.
Before the Algorithm
In December 1986, I was an undergraduate student studying in Madrid for the academic year. Over winter break, a group of us set out across Europe on Eurail passes with no fixed itinerary. Each of us carried either a Frommer's or a Fodor's guide, those thick paperbacks that covered all of Europe in a single volume. We'd board a train, open the book, and, when we weren’t playing euchre, we would spend the ride reading about and debating what to do at the next destination. By the time we pulled into a new city, we had a rough sense of what we wanted to see and a first task: find lodging near the train station.
What happened after that was up to the city. In Paris we did the main tourist attractions and near the Eiffel Tower in the 7th arrondissement we found a street vendor selling the most delicious foot long hotdogs dipped in Dijon mustard and served inside a warmed baguette. In London we found full English breakfast and a great place for fish and chips served in newsprint with all the trimmings. In Amsterdam we wandered through the red light district, young and wide-eyed, taking in the strange theater of it all. The point is that we arrived with minimal plans and very limited knowledge about where to find what. There were no smartphones, no internet, no Ubers, none of what we rely on today.
Greece, Winter 1989/1990
Three years later, during the winter break of the 1989/1990 academic year, I was back in Madrid for graduate school. A friend was studying in Salzburg. We met in Milan and made our way to Greece, spending weeks working through the Peloponnese and the islands: Olympia, Kalavrita, Piraeus, Athens, Crete, and Santorini. We had books, rail passes, and a rough schedule. It suited us fine.
Chania, Crete is where we had one of our most memorable evenings. We ventured into a harbor-side restaurant and ordered braised lamb with local wine. Afterward, walking back through the darkened streets, we came across a group of children kicking a soccer ball around and joined in for a few minutes. Nobody spoke the same language. It didn't matter. At one point one of the children said "Manamana," which anyone of a certain age will recognize from the Muppets. I responded instinctively with the "dodoododoodo," which caught the boy completely off guard and delighted him. It was a very human moment in a faraway place, the kind that no itinerary could have planned, and no algorithm would ever surface.
Lisbon, May 2025
Nearly four decades later, I arrived in Lisbon with something those Eurail trips never had: dozens of hours of advance research. I had used CoPilot, Google, Facebook groups, and recommendations from friends. I had a detailed itinerary with planned visits to specific neighborhoods, viewpoints, and restaurants. A trusted friend had also recommended that I stay in the São Sebastião neighborhood for its residential feel, away from the more tourist-heavy areas of the city. That turned out to be one of the best pieces of advice I received, because it committed me from day one to understanding how the city actually connects on foot.
On one afternoon I climbed the long steep staircase up to the Miradouro da Senhora do Monte and took in the view, then made my way down and navigated toward Rua Rodrigues Sampaio, a street I'd read about for its restaurant scene. The restaurants there looked excellent, but it was a little early for lunch, so I kept walking. And that's when things got interesting.
I turned onto Avenida da Liberdade and stopped to take it all in. It's a wide, elegant, tree-lined boulevard. Upscale shops, outdoor cafes, a median planted with trees and sculpture. I later described it to friends as the Champs-Élysées of Lisbon. Not one of the resources I had used to plan my trip had mentioned it.
I continued exploring, eventually finding my way down Rua de São José, where I stepped into the Igreja de São José dos Carpinteiros, the Church of Saint Joseph of the Carpenters and was captivated by it's beauty. The altar was ornate, and the walls were covered floor to ceiling with elaborate scenes rendered in azulejo tiles, the blue and white Portuguese ceramic panels that you see throughout the country but rarely with this kind of density and artistry. I stood there for a while just looking at the scenes depicted in the tiles.
A few steps further on, on the same street under a different name, I found myself in Largo da Anunciada, a quiet little square, looking up the Calçada do Lavra, one of Lisbon's historic funicular routes climbing steeply through a residential neighborhood that sees very few tourists. Neither had appeared anywhere in my planning. And a little farther down I found Casa do Alentejo, a Moorish-style palace that now functions as a cultural club and restaurant. A friend had recommended it to me a week earlier. I had made a note of it but hadn't planned to go that day. I went upstairs, sat at a table overlooking the beautiful courtyard below, and had a delicious lunch. The room felt like a secret that Lisbon was quietly keeping from its own tourist literature.
That afternoon I pieced together on foot how the Moorish Quarter connects to Avenida da Liberdade, which connects to Rossio, and from there I made my way to Alfama for a planned visit to the São Jorge castle and later to Baixa and Chiado. By the time I was walking back toward São Sebastião, neighborhoods that before my trip had been nothing more than place names on a map had become places I knew, with their own textures and rhythms and vivid memories attached to each of them.
On another day I caught a bus out to the Ajuda National Palace. I arrived at lunchtime and there was nothing to eat in the immediate vicinity. So, I wandered on foot for about ten minutes until I found a tiny bifana place with a terrace across the street. A bifana, for the uninitiated, is a Portuguese pork sandwich, simple and satisfying, the kind of thing you only find if you're willing to wander. I sat on that terrace and had one of the more quietly pleasant meals of the trip.
Two days after my afternoon on Avenida da Liberdade, on May 17th, I found myself swept up in a crowd of Sporting CP fans marching and chanting their way to Praça do Marquês de Pombal to celebrate winning the Primeira Liga title, their second consecutive championship. That only happened because I had learned my way back to São Sebastião from the heart of Chiado and was confident enough in the city to follow the crowd for a while before finding my own way home.
How to Travel This Way
None of this is an argument against planning or against digital tools. Research matters. A good itinerary gives you a foundation and saves you from wasting time on logistics when you could be exploring. But the best version of a travel itinerary is a loose one, with one or two anchored activities per day and plenty of unscheduled time in between.
That open time is where the trip happens. It's where you turn down a street because something caught your eye, step into a church because the door was open, or sit at a harbor-side table and order whatever the kitchen is proud of that day. It's how you come to understand not just the individual places on your list but how a city connects, neighborhood to neighborhood, on your own two feet.
This kind of travel is also easier to do alone or in a small group of like-minded people than it is in a larger group. It requires a shared confidence that the unplanned detour will lead somewhere worth going. In my experience, it almost always does.
Use the tools. Read the blogs, ask the AI, check the groups. Then leave room for the city to surprise you. It will.
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