Pastéis de Nata in Lisbon

A pinch and a punch. January is finally over.

Possibly the longest month I feel like I’ve ever lived through.

Last week, I shared my long-weekend Paris itinerary - one of my favourite winter destinations. And it felt only right that the next itinerary I share is Lisbon.

Those who know me will laugh, because:

a) I’m half Portuguese, and

b) my mum lives just outside Lisbon, in Cascais (don’t worry, I’ll add some bonus tips for there too).

So yes, I may be biased. But I’ve also spent years visiting, eating my way through the city, wandering its hills, and slowly collecting what I think are genuinely solid recommendations. Use them at your own risk.

Now, enough preamble. Let’s get into it.

Lisbon is bright, a little gritty, effortlessly cool and creative. It’s a city where the river keeps appearing at the end of each street, with beautiful tiled buildings on every corner, and where time stretches if you let it. The city rewards slowing down. Wandering. Sitting at a café longer than planned.

So with that in mind, here’s how I’d spend four (or five) days in Lisbon and beyond.

Start gently. Lisbon is deceptively tiring, and there’s no prize for doing too much on day one.

Begin with coffee around Chiado - somewhere like The Folks, Dear Breakfast, or simply a café you stumble into. Then wander downhill toward Baixa, passing the Elevador de Santa Justa. Just admire it from below; save your viewpoints for later.

If you’re up for your first proper stop, hop in an Uber to the Museu Nacional do Azulejo (opening again soon after renovations). It’s slightly out of the centre but absolutely worth it. A perfect introduction to Portugal’s love affair with tiles. Grab a coffee in the museum café before heading back.

Spend the afternoon getting lost in Alfama. Stop for a pastel de nata at Casa São Miguel, wander past the Sé de Lisboa, and let the streets guide you.

As golden hour approaches, make your way to the miradouros (viewpoints). Portas do Sol and Santa Luzia sit just steps apart and are best enjoyed slowly. Sit on the benches, people-watch, listen to live music if you’re there on a weekend, and stay longer than you meant to.

Dinner somewhere traditional nearby, followed by a drink at Palácio Chiado, if you still have energy. Ending your first day in a 19th-century palace feels right.

Optional but highly recommended: a sunset cruise on the river. Lisbon from the water hits differently.

If you plan one day properly, make it this one.

Get an early train from Rossio Station to Sintra. Start at Pena Palace. Yes, it’s popular. Yes, it’s busy. And yes, it’s still worth it. Start early.

From there, head to Quinta da Regaleira. The gardens, tunnels and wells feel slightly surreal, and it’s usually everyone’s favourite.

If you still have energy, continue to Monserrate Palace. Quieter, lush, and often overlooked, but genuinely beautiful.

Have lunch in Sintra town before heading back to Lisbon, ideally with tired legs and a full camera roll.

Start in Belém. Visit Belém Tower from the outside, then queue for Pastéis de Belém. These are the original pastéis de nata, first made by monks at the nearby Jerónimos Monastery in the 1800s. The recipe has been kept secret ever since — which explains both the queue and why it’s still worth it. I go here every time I visit for a warm pastel de nata.

Walk along the river past MAAT, even if you don’t go inside. Lisbon really shines along the water.

Head to LX Factory for lunch and a wander. Browse, eat whatever looks good, and pop into Ler Devagar — it’s one of those places that lives up to the hype.

Later, slow things right down in Jardim da Estrela. A calm, local park that feels like a reset. Sit, read, people-watch.

Spend the evening in Bairro Alto. Shop for souvenirs at places like Embaixada or Amazingstore, then settle in somewhere lively for seafood and wine.

If you have the time, I really recommend adding a day in Cascais. This is where my mum lives, and where I spend most of my time whenever I’m in Portugal — so naturally, it’s one of my favourite places.

It’s an easy train ride from Lisbon and makes a nice change of pace from the city. Start with a walk along the coastal path (the paredão) between Cascais and Estoril. It’s flat, scenic, and one of my go-to walks when I’m here.

Spend some time wandering around Cascais old town. It’s compact, relaxed, and perfect for slow exploring. For lunch, head towards the marina or Casa de Guia for ocean views and casual food.

In the afternoon, walk out to Boca do Inferno to see the cliffs and waves, or explore the Cidadela de Cascais area if you want something cultural without it feeling like a full museum visit.

This day isn’t about packing loads in. It’s more about walking, eating well, and enjoying being by the sea. If Lisbon feels busy, Cascais is the reset.

Lisbon isn’t a city to conquer. It’s one to settle into. Plan Sintra. Loosely plan the rest. Leave space for long coffee breaks, viewpoints that turn into an hour, and wandering without direction.

And if you think this sounds good… don’t even get me started on the Algarve.

Until next Sunday 💌

Tahlia

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