by David McGuffin
Lisbon — Where the Old World Meets the Edge of the Sea
Lisbon is not my most favorite city in Europe, but it does have this crusty, old-world charm that always beckons me to explore its hilltops, back streets, and grand boulevards. The first time I walked through Alfama — the old Moorish quarter draped across Lisbon’s steepest hill — I didn’t want to leave. As the afternoon turned into evening, the vhino verde and vistas would not let me leave. There’s something about this city that feels both ancient and completely alive. It moves at its own pace, it sounds like no other place on earth, and it will feed you extraordinarily well. If you’re going for a few days, you’re in for a treat. Here’s what I’d put at the top of my list.
🏰 Alfama & Castelo de São Jorge
Start at the top, literally. Castelo de São Jorge sits atop Lisbon’s highest hill, a Moorish fortress that has watched over this city for a thousand years. Arrive right at opening — 9AM — and for a brief window, you’ll have the battlements nearly to yourself. The views from up there are the best in the city, a full sweep of terracotta rooftops rolling down to the wide silver ribbon of the Tagus River. And keep an eye out, because peacocks roam the grounds freely, as if they own the place. They might.
On your way back downhill, stop into the Sé Cathedral. It’s Portugal’s oldest church, dating all the way back to 1147, and it looks the part — thick Romanesque walls, a stern facade, built to last through earthquakes and invasions alike. It has.
From there, just wander. That’s really the only instruction for Alfama. The neighborhood is a maze of narrow cobblestone lanes, faded azulejo tiles, and sun-bleached laundry strung between buildings. You’ll get lost. That’s the point.
🚋 Tram 28
At some point, you need to ride Tram 28. Not because of where it takes you, but because of what it is — a rattling, century-old yellow streetcar that hauls itself up and down impossibly steep streets, squeezing through lanes so narrow it nearly brushes the walls on both sides. Locals actually use it, which tells you something. Hang on tight, keep a hand on your pocket, and let it carry you through a slice of the city that most tourists see only from the outside.
🌅 The Miradouros — Lisbon’s Great Viewpoints
Lisbon is built on seven hills, and the locals have turned the best viewpoints into a civic ritual. They call them miradouros, and you need to visit at least two of them. Miradouro de Santa Luzia is the classic — a tiled terrace covered in bougainvillea, with red rooftops tumbling below you toward the river. It’s beautiful, especially in the late afternoon light. But if I had to pick just one, I’d send you to Miradouro da Senhora do Monte. It sits at the highest point in the city, it’s less crowded than the others, and on a clear evening at sunset the sky goes orange and pink and the whole city glows. There are usually pop-up drink vendors and sometimes live music. Grab something cold, find a spot on the wall, and stay as long as you can.
🏛️ Praça do Comércio & the Heart of the City
Walk down to the river, and you’ll arrive at Praça do Comércio — one of Europe’s grandest public squares, opening directly onto the Tagus. It’s framed by elegant golden arcades on three sides and the wide river on the fourth. Stand there for a moment and let the scale of it sink in. This is where Lisbon faces the sea that once made it the center of a global empire stretching from Brazil to India. The triumphal Rua Augusta Arch anchors the opposite end — climb to the top if you want another great view. At golden hour, with the river light bouncing off the buildings, the whole square turns honey-colored and magnificent.
🌿 The Carmo Convent
A short walk uphill into the Chiado neighborhood, you’ll find something I think is one of the most quietly extraordinary sights in all of Portugal. The Carmo Convent is a Gothic church that stands completely roofless — its elegant stone arches open to the sky, with ivy slowly climbing the walls. The 1755 earthquake brought the roof down, and the decision was made to simply leave it that way. There’s now a small archaeological museum inside. But the real experience is just standing in what used to be the nave, looking up at nothing but the open sky framed by eight-hundred-year-old stone. It stops you in your tracks.
⛵ Belém — Half a Day Well Spent
Take the tram or bus about six kilometers west along the river to the district of Belém, and you’re stepping into the heart of Portugal’s Age of Discovery. The Jerónimos Monastery is the crown jewel — a UNESCO World Heritage site and, in my view, one of the most breathtaking buildings in all of Europe. The style is called Manueline, Portugal’s own ornate maritime Gothic, and the stonework is almost unbelievably intricate — ropes, anchors, armillary spheres, and exotic flora carved into honey-colored stone. Vasco da Gama is buried inside. Buy your tickets in advance; the lines get long, and there’s no shade. Right next door, at the Pastéis de Belém bakery, order a warm custard tart straight from the oven, dust it with cinnamon, and eat it standing up. The recipe is a closely guarded secret that hasn’t changed since 1837. It’s worth the trip to Belém for that tart alone.
🎶 Fado — Don’t Skip This (but on my tours we do Fado in Coimbra)
On one of your evenings, find a small restaurant in Alfama where the lights are low and the chairs are pushed close together. When the fadista takes the floor and begins to sing — accompanied only by the Portuguese guitar — the room goes completely silent. Fado is the music of this city: born in these very streets, full of longing, salt air, and something irretrievably lost. Whether you understand a word or not, it will reach you. This is one of those experiences that no amount of reading about it can prepare you for. You just have to go.
🍽️ Eating & Drinking
Lisbon’s food culture will not let you down. Start every morning with a pastel de nata — a warm custard tart — and a bica (a small, strong espresso) at a neighborhood café counter, standing up like a local. For lunch or dinner, look for grilled fish, garlic prawns, or the beloved bacalhau (salt cod) prepared in one of what locals claim are 365 different ways. The wine is excellent and inexpensive — a crisp Vinho Verde on a warm afternoon, a robust Alentejo red with dinner. Small family restaurants are the best bet. Tip generously at the good ones; they deserve it.
💡 One Last Thing
The best tip I can give you for Lisbon doesn’t involve any monument or restaurant. Buy a small bag of ginjinha cherry liqueur chocolates from a street vendor near Alfama, find a set of steps on any hill, and sit down. Watch the light change over the rooftops. Let the city come to you. Lisbon has a pace all its own — unhurried, warm, a little melancholy in the best possible way. The sooner you surrender to it, the better your trip will be. I promise you, you won’t want to leave.
