Wander the Alfama District
Start your Lisbon trip the right way by getting lost. Alfama doesn’t follow any grid or plan. Instead, it winds and circles, full of corners where time doesn’t seem in a rush. This is the city’s oldest quarter, and you feel it underfoot: uneven cobblestones, low arches, steep stairs that lead to silence or maybe a courtyard with laundry flapping in the breeze.
Every turn offers something new, or very old. Tiled facades in blues and greens cling to crumbling walls. Locals poke their heads out of tiny doorways. Maybe you’ll stumble on a pocket sized cafe where the chairs don’t match and the espresso is strong.
And then there’s the music. At night, or even in the late afternoon, you might hear Fado the sound of longing, of Lisbon’s soul spilling from inside a tasca. Follow it. These moments don’t show up on maps.
Climb to the Top of São Jorge Castle
Perched above the Alfama district, São Jorge Castle isn’t just a historic fortress it’s one of the best spots in Lisbon to get your bearings. The sweeping views from the ramparts stretch across red rooftops, church towers, and the wide, glinting Tagus River. It’s where you start to understand the city’s layout hills, staircases, and all.
Walking the castle walls means stepping into centuries of layered history. The Romans built foundations here. The Moors expanded it. The Portuguese kings turned it into a royal residence. You’ll find a mix of excavation zones, battlements, and leafy courtyards that tell bits of each chapter.
Getting there on foot means a decent uphill hike nothing brutal, but enough to break a sweat if it’s warm out. Not feeling it? Catch the iconic Tram 28 and let it haul you most of the way. Either way, the payoff at the top is worth every step.
Enjoy a Sunset from Miradouro da Senhora do Monte
If you’re looking for a view that earns your silence, head to Miradouro da Senhora do Monte. Tucked away in the hills of the Graça neighborhood, this spot offers one of the most sweeping panoramas of Lisbon red rooftops, the winding Tejo River, and the castle all in one line of sight. It’s no secret to locals, but somehow still flies under the radar with tourists, meaning you’ll find more sky than selfie sticks.
The vibe here is laid back. A few benches, maybe a musician playing soft guitar, and a golden hue that hits just right as the sun dips. Bring a bottle of water or a cold Super Bock, grab your camera, and let time slow down. For vlogging, golden hour here is practically cheating it’s cinematic by default.
Taste Traditional Portuguese Dishes with a Modern Twist
You’ll be tempted to grab the first pastel de nata you see and honestly, even the average one is pretty great. But hold out for the bakeries with lines of locals, or the ones that sell out by noon. The good stuff is warm, barely holds its shape, and makes you stop mid sentence.
Beyond pastries, Lisbon is leaning hard into a movement that respects the classics but isn’t afraid to remix them. Think bacalhau with chef y flourishes, octopus charred to perfection and served with unexpected sides, or piri piri chicken elevated without losing its heat. You’ll find plenty of small restaurants doing this quietly and well usually off the main drags, usually worth the detour.
If you don’t want to gamble your stomach on guesswork, book a food tour. A good local guide will steer you wide of overpriced tourist menus and straight into backstreet tascas making meals the old school way or the new school way with soul. Consider it a crash course with less wandering and more wine.
Visit the MAAT and Belém Cultural District
For design and architecture nerds, MAAT is reason enough to cross the city. It’s sleek, forward thinking, and perched dramatically on the riverbank. The building itself is a statement. Inside, expect a mix of contemporary art, tech focused exhibits, and bold design experiments. It’s the kind of place that makes you rethink what a museum should be.
Just a short walk away, shift gears and dive into Lisbon’s deep past. The Jerónimos Monastery stuns with its intricate stonework and soaring cloisters Portugal’s Age of Discovery written in limestone. Belém Tower, equally iconic, once guarded this stretch of coastline. It’s photogenic, sure, but it also echoes centuries of turbulent maritime history.
And yes you can’t leave Belém without tasting the original Pastéis de Belém. There’s a reason the line wraps around the block. Buttery, flaky, warm from the oven. Worth every minute of the wait.
This pocket of Lisbon nails the mix: bold design, layered history, and a pastry that will ruin all others for you.
Ride Tram 28 But Strategically
Tram 28 is Lisbon’s most iconic ride and also its most overcrowded if you go at the wrong time. Your best bet? Aim for early morning or just before sunset. That’s when the tram still feels like a small glimpse into old Lisbon, not a rolling photo op jam packed with tourists.
Don’t just ride it from end to end. Hop off where it feels right. Maybe it’s a quiet street in Graça, or a sunny square in Estrela. Some of the city’s best moments hide outside the main guidebook bullets and Tram 28 glides right past them if you’re not paying attention. So use the tram as a frame for your own route. Ride, step off, look around. You’ll catch the rhythm of the city better that way.
Consider a Quick Escape to a Romantic Small Town
Lisbon makes the perfect launchpad for quick getaways that show off Portugal’s quieter, more intimate side. In under an hour, you can find yourself wandering the fairy tale palaces of Sintra or soaking up the coastal calm of Cascais both easy do it in a day destinations by train.
But the real finds lie a bit further off the radar. Towns like Óbidos with its whitewashed lanes and literary flair, or Évora with Roman ruins tucked among sun drenched wine country, deliver big on charm without the crowds. Even places like Azeitão or Monsaraz blend history, nature, and a slower pace that contrasts with city buzz.
If you’ve got time and a loose itinerary, use Lisbon as your anchor and plan for a couple of day trips. They’ll add depth to your trip and a few extra layers to your footage if you’re vlogging it. For more inspiration, check out Europe’s Most Charming Small Towns You Need to Visit.
Final Tip: Wear Comfortable Shoes
Here’s the truth: Lisbon is not a flat city. Its famous seven hills aren’t just quaint they’re a workout. And those beautiful mosaic sidewalks? They’re slippery when wet and tough on thin soles. Style matters, sure. But if you pack only sandals or flimsy flats, your feet will complain by midday.
What you need is a solid pair of stylish sneakers something with cushion, grip, and stamina. You’ll be walking up steep alleyways, down cobbled stairs, and across plazas that look like street art. Good shoes aren’t optional here; they’re the difference between cutting your day short or staying out for one more miradouro sunset.
Lisbon rewards the curious. Just make sure your feet can keep up.