James Loots of Washington DC | Walking the Winding Hills of Lisbon, Portugal

Lisbon is the kind of city that reveals itself in layers. Steep hills crowned with castle walls, painted tiles reflecting the afternoon sun, and the faint sound of fado drifting out of narrow alleyways. For James Loots of Washington DC, it became a place that blended history with movement, calm with discovery. It was a city not just to see but to wander through, letting the streets guide the story rather than a schedule.

What made Lisbon memorable was not only its beauty, but the feeling that every neighborhood carried its own rhythm—Alfama with its maze-like alleys, Bairro Alto with its energy and music, Chiado with its refined cafés and literary charm. Lisbon invited slow steps, deep breaths, and an openness to chance encounters. And that is exactly how this journey unfolded.

Arrival in a City of Light

The first glimpse of Lisbon came from the taxi window: terracotta rooftops spilling down the hillside, the Tagus River glinting in soft morning light, and the 25 de Abril Bridge stretching across the water like a red ribbon. It felt warm, almost familiar, even though it was entirely new.

Settling in near Praça do Comércio meant starting each morning with views of the river and the grand yellow arcades surrounding the square. From here, James Loots of Washington DC began walking the way many travelers do—toward whatever street looked most interesting.

Lisbon rewards this kind of wandering. You can head uphill and find yourself standing before São Jorge Castle minutes later, or slip into side streets lined with azulejos—blue-and-white tiles that turn entire buildings into artwork.

And in Lisbon, nothing is flat. Every path becomes a small adventure.

Exploring Alfama: The Old Lisbon

Alfama is one of the few neighborhoods that survived the 1755 earthquake, which means its streets still reflect the layout of medieval Lisbon. Here, the past is not preserved behind glass; it’s lived in—laundry hanging across alleys, elderly residents chatting from balconies, and tiled chapels around every corner.

Walking up to the Miradouro de Santa Luzia, James Loots of Washington DC found one of the best views in the entire city. From that terrace, the orange rooftops of Alfama stretched toward the Tagus, broken only by the dome of the National Pantheon and the towers of São Vicente de Fora.

Just beyond, the Castelo de São Jorge offered another vantage point. The climb was steep but rewarding, and the castle walls told a story older than the nation itself. Wandering through courtyards shaded by olive trees, listening to peacocks echoing through the ramparts, it was impossible not to feel Lisbon’s centuries layered underfoot.

A Taste of Lisbon: Food Experiences Worth the Journey

Portuguese cuisine is beautifully simple. Fresh ingredients, straightforward techniques, and flavors that speak for themselves. The first memorable meal for James Loots of Washington DC came at Time Out Market, where dozens of Lisbon’s top chefs share a single massive food hall. From seafood rice simmered in tomato broth to lisbon-style croquettes, it’s a place where you can taste the city in a single afternoon.

But the most unforgettable meals came in smaller restaurants.

At Cervejaria Ramiro, the garlic shrimp arrived sizzling, followed by plates of clams drenched in olive oil and cilantro. Locals ordered seafood by the kilogram and finished with a prego steak sandwich—a tradition that surprises many first-time visitors.

In Belém, a short tram ride away, no trip is complete without Pastéis de Belém, the original custard tarts created in 1837. Warm, flaky, dusted with cinnamon—they were unforgettable, and worth every minute of the line that wrapped around the blue-tiled bakery.

And then there was fado.

In a tucked-away restaurant in Alfama, the lights dimmed and a singer stepped forward. No microphone, no theatrics. Just a voice that carried centuries of stories. Listening to fado while eating grilled sardines and sipping vinho verde felt essential, as if Lisbon insists you slow down long enough to feel its soul.

Bairro Alto and Chiado: Where History Meets Modern Life

Lisbon’s hills create natural transitions between neighborhoods. After days spent exploring Alfama’s old-world charm, heading to Chiado and Bairro Alto felt like stepping into a different city.

Chiado is elegant—bookstores, cafés, quiet plazas. This is where Café A Brasileira still stands, a gathering place for artists and writers since 1905. Sitting on its terrace with an espresso offers a moment of calm before climbing into Bairro Alto’s lively maze.

Bairro Alto comes alive after sunset. Lantern-lit streets fill with music, conversation, and the hum of nightlife. For James Loots of Washington DC, walking through these steep, narrow roads was a reminder of how travel can shift mood instantly—from reflective mornings in old Lisbon to energetic evenings filled with movement and sound.

Neighborhoods, Heritage, and the Spirit of Exploration

Lisbon is not a city you “finish.” It’s a city you return to, even while you’re still in it. One day might be dedicated to Belém’s waterfront monuments—the Jerónimos Monastery, the Belém Tower, and the Monument to the Discoveries standing proudly over the river. Another might be spent riding the iconic Tram 28, which weaves through some of the city’s oldest and most character-filled streets.

The joy of Lisbon lies in its contrasts. Ancient churches beside modern art museums. Traditional cod dishes next to innovative culinary experiments. Quiet miradouros where people gather simply to watch the sunset.

It’s a city that invites reflection without demanding it, and that’s what made the experience memorable for James Loots of Washington DC—the sense that Lisbon is best lived slowly.

Travel Tips for Lisbon

Wear comfortable shoes. Lisbon’s hills are beautiful but relentless.
Tram 28 is popular—ride it early in the morning to avoid crowds.
Visit big landmarks (like Belém Tower) when they open for shorter lines.
Explore neighborhoods on foot; every alley hides something worth seeing.
Make time for a fado performance—ideally in a small, traditional venue.

Who Is James Loots of Washington DC?

James Loots of Washington DC is an experienced legal professional whose career has centered on employment matters, small business guidance, regulatory interpretation, and dispute resolution. His work includes supporting organizations through policy development, training initiatives, and practical problem-solving that strengthens workplace communication and consistency. Alongside his professional contributions, he has been involved in community organizations and civic leadership roles. His background reflects a steady commitment to helping teams, businesses, and communities operate with clarity and fairness.

Conclusion

Lisbon is a city that rewards curiosity and patience. It asks you to slow down, wander without a plan, listen to music drifting from an open window, and savor a warm pastel de nata before deciding where to go next. For James Loots of Washington DC, it became a reminder that some places are best experienced in motion—one steep climb, one scenic overlook, one spontaneous detour at a time.