This last trip was actually my second to Portugal’s capital city, and whilst I’ve written about my previous trips to Portugal here and here, I realise I’ve never written specifically about Lisbon itself, so I’m rectifying that now!

We love the city, it was the destination for our first holiday together, and it’s where we’re currently planning to get married (exciting times!)

I’d be hard pressed to say exactly what I love the most: The food is great, the weather is delightful, there’s greenery, beautiful architecture, culture and heritage everywhere you look – and their pastries are mind blowing!

In terms of things to do in Lisbon, I’ve listed 8 of my highlights for the city itself, plus two places you simply cannot miss that are just outside the city:

1. Get lost in Alfama

These are the winding little cobbled streets and terracotta roofs featured in every guidebook. Quintessentially Portuguese, you can just wander and see something different on every corner. The Cathedral (Se) that towers over this district is a focal point and worth a wander around (take a tram if you don’t fancy the steep walk up!) People are friendly, there are lots of little shops and restaurants scattered throughout the streets, but for us the best time to visit was in the evening, when we were to Clube de Fado for dinner and live fado performances (see next point!)

2. Experience live fado

Fado music is hauntingly beautiful. Normally there are two people performing – one guy on a mandolin or Portuguese guitar and a woman singing (although it sounds more like wailing and moaning a lot of the time). The songs are melancholy love songs, and the passion and emotion of the songs is expressed by both the singer and the musician – it’s completely captivating. If you watch a show with dinner, you’ll find that food is served in the breaks between performances (I’m sure if it wasn’t the food would be neglected and go cold!) There are lots of places you can experience fado, in Alfama and in Chiado (and across Portugal), we picked Clube de Fado and had a great experience.

3. Head to Belem first thing in the morning before the crowds

Check out Torre de Belem (we didn’t queue and pay to go in, we were happy to see it from the shore), wander along the riverfront to check out the sculpture and see the 25 Avril Bridge. Cross the road to visit the Monasterios de Jeronimo, which is even more impressive inside, with intricately carved woodwork, spiderweb ceilings and beautiful stained glass windows. Continue down the small street of shops and cafes – DO NOT miss Pasties de Belem – their pastel de nata (Portuguese egg custard tarts) may be the best we’ve tasted – just make sure it’s not too late in the day otherwise you’ll struggle for a table and the takeaway will be queuing out of the door!

4. Have lunch in Cais do Sodre 

We did this after out morning in Belem – we walked along the streets a bit further until we reached the bridge (from where we could see the huge Christ the King statue over the river in Cacilas) and caught a train (it had started raining and was a long walk!) to Cais do Sodres. Here we followed recommendations and went straight into the indoor market – Mercado da Ribeira on one side (full of local produce) and the Time Out Lisbon Market on the other side (full of amazing food outlets and drinks stalls, and with a buzzing atmosphere). Next time I would try and get here a little earlier as we struggled to find any bench or table space.

From here we walked up the back streets, away from the train tracks and up some seriously steep streets to Santa Catarina (we would have taken the cable car but the queue was huge!) The steps were tough work but it was worth it, at the top we had a rest stop in Noobai – an open air wine and cocktail bar with great views over the river– before moving on to the Pharmacia bar. This was a very cool bar located in the front garden of the Medicine Museum – great for watching the world go by from deck chairs, with drinks themed around medication and prescriptions.

5. Eat and shop in Chiado

Make sure you pop into Convento do Camo while you’re there and see the impressive gothic convent ruins. If you happen to follow recommendations 3 and 4 above, you can easily walk to Chiado from Santa Catarina, especially if you’ve rested and refreshed yourselves in the bars there!

Chiado is the more refined area of Lisbon, with higher end shops and nice restaurants – we had heard lots of good things about Belcanto restaurant but unfortunately we couldn’t get a reservation. If you’re heading that way, you should definitely call into Convento do Camo – it’s doesn’t take long to wander round and admire the ruins of the convent and the ribcage-like arches that remained following the earthquakes that destroyed much of the city. From the back off the convent, you can take the beautiful antique Elevador de Santa Justa down to the tourist centre of Baixa (or walk the stairs and take a regular lift like us if you don’t want to queue) down to the main streets of Baixa and Rossio below. (There’s also a great rooftop bar – TOPO – on the back of the Convent).

6. Taste ginjinha

There are lots if places you can taste the delicious sour cherry brandy drink, but the best place has to be its original spot in the pedestrian streets of Rossio – A Ginjinha Bar. Here, you literally buy a shot over the counter on the street (choose with or without cherries) and drink there and then in the streets. Perfect as an aperitif as it’s on the way to all the restaurants in Rossio.

7. Have a night out in Bairro Alto

We’ve only done this once (must be getting old) when we went for dinner in the highly rated 100 Maneiras before moving onto its bistro cousin for cocktails afterwards. The area has a bit of student feel (again, maybe I’m just getting old!) and was definitely a late night place, where people were hanging out drinking and smoking on the streets late into the night.

8. Wander the Castle ramparts

This is one thing we haven’t done yet! Next time we visit, we’ll be sure to head up to Castelo de Sao Jorge and wander around the ramparts – apparently you can take the tourist Tram 28 up there, and there is a fantastic wine bar at the top which is great spot for a sundowner – Wine Bar do Castelo – and offers more than 150 Portuguese wines by the glass!

9. Take an unforgettable day trip to Sintra

This beautiful green spot is the stuff of fairytales, with spectacular castles and forts, overgrown ruins, lush green forests – and yet more delicious pastries!

Here, I would recommend walking from the pretty little village centre out to Quinta Da Regaleira and enjoying a morning wandering around the ruins and greenery. If you do go, make sure you go down the dark winding steps of the wells that take you underground through tunnels to behind the waterfall.

I’d also recommend an afternoon at Pena Palace and Park, and a gentle meander from there down to Castelo dos Mouros. Definitely get a tuk tuk from the village centre up to the brightly-coloured palace though, it was a last minute decision for us, but we were so glad we did!  We overtook hundreds of cars, some of whom had apparently been queuing for two hours to get up the narrow steep streets to the palace – our little tuk tuk zipped past them all! (Apparently this congestion only occurs in peak summer months however). Buy tickets online if you want to take a look inside the castle without queuing, although it’s worth knowing you can access most of the castle without a ticket (personally, we weren’t too fussed about seeing the interiors). It’s a short walk back down the road to Castelo dos Mouros (the Moorish Castle) where you can walk along the ramparts and through the forest to get to the castle. We chose to hike back down and give ourselves some exercise (although I was glad we hadn’t chosen to hike up too when we saw the seemingly never-ending steps of the route!)

Back in the village, there are lots of great places to eat tapas and drink wine, and lots of cute little shops and gelateries, plus another fantastic pastry shop – Piriquita – which makes delicious travesseiros – the local Sintra pastry – best eaten in the plaza in front of the palace, Palacio Nacional de Sintra.

Next time we visit, I’m keen to head to Monserrate Palace and Park, and also Convento dos Capuchos (the Cork Convent) but these will need a car/taxi ride, and we just couldn’t squeeze in the time on our last trip.

From Sintra, it’s only ten minutes to Estoril on the coast, where there is the famous Casino Estoril, the largest casino in Europe, that was supposedly where Ian Fleming got his inspiration for the character of James Bond – and where parts of the film On Her Majesty’s Secret Service was filmed. You can also rent bikes for free here and take them out to explore the coastline. Another one for another time for us!

10. Have a beach day in Cascais

This was the only place that I felt didn’t quite live up to expectations. It’s the seaside refuge for the Portuguese royal family, made up of three beach areas. There’s an old town of cobbled streets, pubs, restaurants, cafes and shops. The beaches in the centre of town were quite small, and the town itself was very touristy, with the cobbled squares full of English and Irish pubs.

It makes a nice change from the city however, and if you are going to visit, there are a couple of places you should go. First things first, fuel up with a delicious ice cream from Gelados Santini. Take a wander around the Citadel, there’s a luxury hotel, the Pousada Cascais and several impressive art installations. Head towards the sea and over the ramparts and you’ll be able to wander through the marina. From here, it’s only fifteen to twenty minutes along the coast to the Boca do Inferno(the Mouth of Hell). Here the water is rough and pounds against the cliffs and rock formations, there’s a little handicrafts market and a nice seafood restaurant, Restaurant Mar do Inferno (make a reservation in advance though as they get booked up).

It’s no surprise that this has turned out to be one of my longer blog posts, and I am incredibly excited for our next trip back – although that may be to do with slightly more than the city itself!!