A winter city break to Lisbon

Portugal’s a go-to for summer holidays and even its capital city, Lisbon, is the perfect combo of beachy and urban. So, when I booked a last-minute winter city break, I wasn’t expecting there to be much going on… I was wrong.  

Lisbon has so much soul, and that doesn’t change with the seasons. The winding cobbled streets lined with colourful buildings, the soundtrack of bicycle bells and buskers – it serves up serious charm all year round.  

Here’s what I got up to on my wintery weekend away to Lisbon…  

Day 1 – arrival in Lisbon  

We arrived on a Friday afternoon in early December, the air crisp but refreshing. After dropping off our bags at our stay, the first thing we did was try a pastel de nata. We saw a queue at Manteigaria and had a feeling it must be good. We were not wrong. The pastry was flaky and the custard melts in your mouth – don’t forget to sprinkle on icing sugar and cinnamon for the whole experience. Plus, the glass wall where you can watch a constant stream of tarts being made by hand is a lovely touch. They were so good, I had to have two… I don’t think I’ll ever understand how you could live here and not eat these every day. 

As we left the shop the sun was starting to set, so we decided to explore the city with what was left of the light. Now, as much as I love Lisbon, if there’s one thing I could change it would be the hills. They. Are. Everywhere. Walking around the centre is a whole workout. But there’s another option – the streets are filled with tuktuk drivers braving the inclines to cycle tourists to all the must-see spots. So, on we hopped to see all the main viewpoints of the city. Our driver was a lot of fun and managed to squeeze so much into our 90-minute ride. I’d 100% recommend seeing the city this way, especially in the evening as we saw the sun set then watched the lights come on across the city below. 

After a tip from a local, we strolled to Wonderland Lisboa – a Christmas market. The whole place was covered in fairy lights and filled with stalls selling everything from food to local crafts. We drank mulled wine and ate fresh fish and seasonal snacks. The vibe was super festive – what a way to spend our first evening. 

Day 2 – monasteries, markets and music 

The next morning, we were determined to fit in as much as possible, so we were up and out early to get Tram 28 to Bélem. I’ve heard getting a spot on this in the summer’s a nightmare, but fewer tourists in the winter meant we even got a seat. Definitely an activity to tick off the Lisbon bucket list! 

We were conveniently dropped right outside Pastéis de Bélem, a café selling custard tarts that are so good they have their own name. To say this breakfast was life-changing might be an overstatement, but I’m going to say it anyway. These tarts will forever live rent-free in my head. I can’t even begin to describe them, so you’ll simply have to go try them yourself. Heavenly. 

Next door is the Jerónimos Monastery. Grab your joint Monastery and Tower tickets and join the queue – it’s busy all year round, but it moves fast and it’s totally worth it! The Portuguese-Gothic architecture dates back to the 1500s, then a short walk away is the infamous Belém Tower, which has views of the Tagus River.  

We’d built up an appetite after all our sightseeing, so we took the tram back into town to grab a bite to eat. One of my friends had recommended Hygge Kaffee to me, and it did not disappoint. It’s a cute café that does all day brunch and lunch, the perfect place to rest and refuel for the afternoon.  

My friend and I love a bargain, and considering Lisbon’s flea market, Feria de Ladra is rated the second-best in Europe, we weren’t leaving without making a pit-stop. There was an endless number of stalls selling a huge variety of second-hand items, from denim jackets and vinyl to fine China teacups. If you’re happy to rummage, I guarantee you’ll find some major deals here. 

To continue our market tour, we got the bus over to Lx Market – but don’t be fooled, you won’t find anything second-hand here. It had a more boujie, fashionable vibe, lined with boutique shops and upmarket bars. The market itself’s in a converted warehouse, filled with local up-and-coming designers showcasing their latest creations. On the roof, you can sit out with a drink and enjoy a view of the impressive 25 de Abril suspension bridge that connects Lisbon to Almada across the river. 

A Saturday night in Lisbon isn’t complete without a trip to Barrio Alto, the centre of the city’s nightlife scene. Even in the winter, the pavements outside the bars were overflowing with people having a good time, most huddled around an old barrel serving as table for their wine glasses. The area was lit up by gorg Christmas lights, adding to the festive atmosphere. We picked Portas Largas, which served up live music, authentic nibbles and a cosy tavern vibe. Chatting to the friendly locals, we loved getting stuck into the local culture while we drank Portuguese wine and beer.  

Day 3 

On Sunday morning, we were trying not to think about going home while we packed our bags ready for our afternoon flight. There was still a bit of time for a final explore, so we started at Neighbourhood, a well-recommended brunch spot. A special mention goes to their famous breakfast burrito, toasties and yum coffee.  

Our last activity on the checklist was to visit the São Jorge Castle, which sits on a hill overlooking the city. With panoramic views of Lisbon, it’s a great way to wrap up the weekend and see all the areas we visited. The castle itself is straight from a fairytale, with tall towers and arched windows. We strolled around and read all about its cultural significance and how it protected the city over the years. And with that, our Lisbon trip was finito (after filling up my carry-on with pastel de nata for the journey home, ofc). 

We packed a lot into our 48 hours here, but we definitely didn’t get to everything. My main thought on the flight home was that I’m determined to go back and see more of what this beautiful city has to offer. There’s something different around every corner, so make sure you do some research but also leave room for spontaneous stuff – you’ll come across plenty of hidden gems.  

So go, book those flights! You don’t have to wait for summer – Lisbon’s for everybody, all year round. 

You heard her – check out our Portugal deals to lock in a trip to Lisbon this winter.  

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Author: Mia Casey (she/her)
Last updated: 20/08/2025