Lisbon, Sintra & Cascais in Four Days

Day 1 - Hills and Miradouros

We arrived at our hotel in Chiado, one of those neighborhoods that instantly feels right—central, lively, and perfectly walkable. After dropping our bags, we headed straight to Breakfast Lovers Chiado for breakfast. A quick reminder: don’t forget to make reservations—Lisbon gets busy fast.

Fueled and ready, we made our way to Praça do Comércio, the city’s main square. Open, grand, and right by the water, it truly feels like the heart of Lisbon. Standing there with the river in front of us, the city immediately pulled us in.

For the rest of the day, we decided to do what Lisbon demands: climb uphill. We headed toward the city’s famous viewpoints, stopping at Miradouro de Santa Luzia and Miradouro da Graça (Alcântara). Tile-covered walls, orange rooftops, and endless views over the river—every stop felt like a reward after a steep walk.

Along the way, we made our way up to São Jorge Castle, where Lisbon opened up beneath us. And yes—inside the castle grounds there were peacocks casually wandering around, adding a slightly surreal touch to the whole experience. After all that climbing, we found small spots selling piña coladas, and of course, we stopped to try one. Cold, refreshing, and very much needed. Instant relief.

We continued exploring the city, visiting the Carmo Archaeological Museum, passing by the iconic Santa Justa Elevator, and making our way to Lisbon Cathedral (Sé de Lisboa). Right next to the cathedral, a lively local market/fair was set up, which we wandered through—full of stalls, music, and local energy.

It was a very hilly, very walk-heavy day.

Naturally, we stopped by Manteigaria to try our first pastel de nata—warm, crispy, creamy, and absolutely worth the hype.

We ended Day 1 with seafood for dinner, letting the day slowly settle after hours of walking, climbing, and taking in views.

Lisbon greeted us with hills, peacocks, pastel de nata, and piña coladas—and honestly, what a start.

Day - Belém Classics

We started Day 2 with breakfast at The Folks Chiado, easing into the morning before heading out. First stop was just around Misericórdia, where we watched Lisbon’s famous yellow tram pass by—one of those classic scenes you’ve seen a hundred times but still stop for.

From there, we headed west toward Belém. And of course, we couldn’t skip Pastéis de Belém. Fresh, warm, and perfectly creamy—trying them straight from the source really does hit different.

Fully satisfied, we began exploring the area: Belém Tower, standing proudly by the water; the Padrão dos Descobrimentos (Monument to the Discoveries) with its impressive scale; and the nearby Jerónimos Monastery, calm, detailed, and endlessly beautiful.

After soaking in Belém, we followed the coastline, walking along the water and eventually spotting Ponte 25 de Abrilstretching across the horizon. The view alone was worth the walk.

From there, we made our way to LX Factory—industrial, creative, and full of energy. Shops, cafés, street art, and that effortlessly cool Lisbon vibe.

Before heading back for dinner, we squeezed in a walk through Alfama. Narrow streets, tiled walls, laundry lines, and that quiet, lived-in atmosphere—Alfama feels like Lisbon at its most authentic.

Before heading back toward Chiado for dinner, we took a break at Jardim da Estrela. After a full day of trams, walking, and sightseeing, it was exactly what we needed. Sitting on the grass, watching locals walk their dogs and kids run around, we finally slowed down for a moment. Quiet, green, and effortlessly local—Jardim da Estrela felt like Lisbon letting us catch our breath before the evening continued.

In the evening, as we returned closer to Chiado, we chose Honest Greens for dinner. We already knew the brand from Barcelona, so it felt familiar and comforting. Healthy bowls, fresh flavors, and exactly what we needed after a full day out.

We ended the day with matchas on the terrace, watching the sunset and letting Lisbon slow us down—finally.

Day 3 - Sintra

Day 3 was our Sintra day trip. We started the morning with breakfast at Liberty, where we tried something new for the first time: syrniki. We later learned the place is run by a Ukrainian owner, and those soft, slightly sweet pancakes instantly became one of our favorite breakfasts of the trip.

After that, we headed to the train station and reached Sintra easily by train—simple, smooth, and very travel-day friendly.

On this day, we mostly used Uber to get around the city. It was easy, affordable, and honestly very convenient—especially when energy levels were low.

That said, Sintra also has tuk-tuks, which you’ll see everywhere, especially in hilly areas and tourist spots. They’re a fun option and can be useful for short distances, but prices vary, so it’s always good to agree on the cost beforehand.

Originally, the plan was ambitious: Quinta da Regaleira, Pena Palace, and the Moorish Castle all in one day. But travel has its own rules. I had already been feeling unwell during the Lisbon part of the trip, and that day, the sickness fully caught up with me. While everyone else was walking around in tank tops, there I was in long sleeves, trying to keep going.

So we adjusted. And honestly, it was the right call.

We focused entirely on Quinta da Regaleira—and it felt like stepping into another world. The estate is pure magic: lush greenery, hidden paths, caves, tunnels, and a sense that something symbolic is always just beneath the surface. It doesn’t feel like a place you simply visit; it feels like a place you experience.

The highlight, without question, was the Initiation Well (the round tower). Descending into it felt symbolic—like a journey into the unknown, into the unconscious. Stone steps spiraling downward, moss-covered walls, dim light filtering from above. Quiet, powerful, almost meditative. If Sintra has a soul, it lives there.

After Regaleira, we wandered through Sintra town, keeping things light and slow. We tried cherry liqueur (ginjinha)—served in a tiny chocolate cup, sweet, strong, and comforting. Exactly what the moment needed.

By the time we returned to Lisbon, energy levels were low, so dinner stayed simple. Near Praça do Comércio, we grabbed slices of pizza and fries and ate them by hand. No reservations, no long dinners, no pressure.

Because sometimes, after a long journey—and especially when you’re sick—rest is part of the travel too.

Sintra deserved more time. And so did we. But even like this, it stayed unforgettable.

Some Sintra Tips:

• Pick one or two main sights—trying to see everything in Sintra in one day is exhausting.

• Wear comfortable shoes and bring layers; the weather changes quickly.

• Book tickets in advance when possible, especially in high season.

• And most importantly: listen to your body. Adjusting plans doesn’t ruin a trip—it reshapes it.

Day 4 - Cascais Air and Oceans Views

Day 4 was our last day in Portugal, and we planned a day trip to Cascais. We started the morning with breakfast at Zenith—a familiar favorite we already knew from Barcelona. Comfort food, good coffee, and a relaxed start to the day.

The ocean air in Cascais was instantly refreshing. I was finally feeling much better, and it showed—we walked a lot, happily. We wandered through the marina, passed by a few small museums, and just let the town set the pace.

The atmosphere in Cascais felt completely different from Lisbon. Right by the ocean, people were swimming, sunbathing, and hanging out without a rush. Old-school cars passed by with loud music playing, adding to the slightly chaotic but very alive energy of the place.

Our main destination was Boca do Inferno—and honestly, we were mesmerized. The waves crashing against the cliffs, the sound of the ocean echoing through the rocks, the endless blue. Dramatic, powerful, unforgettable.

After that, we slowed things down at another branch of Honest Greens, sipping kombucha on the terrace while waiting for our return train. Cool breeze, tired legs, and that quiet satisfaction of a day well spent.

And then came the surprise of the day. For our final dinner, we went to an open buffet place—and discovered something completely new: white wine sangria. Light, refreshing, slightly fruity… and instantly a favorite. One of those unexpected travel discoveries that stay with you long after the trip ends.

Cascais was the perfect goodbye: ocean air, dramatic cliffs, slow walks, and a glass of something we’d never tried before.

Portugal, you were very good to us.