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  • Writer's pictureJen Williams

My Top 3 Lisbon Highlights

Updated: Dec 3, 2019

Back in September of last year, I embarked on my third solo trip and ventured to the gorgeous city of Lisbon! While Portugal had never been one of my bucket list nations, I had fallen in love with Lisbon over the previous few months (thanks to instagram) and decided it would be the perfect place to spend a week away from the office.

While I love travelling to places I’m already crazy about and have extensively researched, Lisbon was relatively unknown to me, and so I was able to appreciate the city with an open mind. I had a short list of things I wanted to see and do and, as always, the places I enjoyed the most (or least!) weren’t necessarily those I had expected! That being said, here are my top 3 highlights from the week I spent in Lisbon.

Female travel blogger in Praça do Comércio, Lisbon
In Praça do Comércio on my first day in Lisbon

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1) Sintra: Pena Palace & Quinta da Regaleira

I know what you’re thinking - item number one and I’ve already strayed from the city itself! Correct! But, just a 40-minute train ride from the centre of Lisbon, Sintra is the perfect distance from the capital for a day trip. If you have two or three days to spare, however, I would highly recommend spending a bit more time in Sintra, allowing yourself to appreciate everything it has to offer.

I ventured to Sintra on my final full day in Portugal, catching the first train from Lisbon with bus timetables, maps, and my plan of action in hand. My #1 goal was to visit the iconic and gram-worthy Pena Palace, and hopefully have time left to visit the Quinta da Regaleira and Monserrate Palace….but two out of three ain’t bad, right?

While my pre-trip research was minimal, I had spent some time looking at how best to get around Sintra in order to make best use of my day there. You’ll find a lot of mixed reviews about the buses in Sintra, but I hoped for the best and made sure I knew where I was going beforehand, starting the queue for the first 434 bus to Pena Palace from Sintra station.

If you don’t mind a bit of queueing, and (very) possibly not having a seat, the buses in Sintra aren’t dreadful. They aren’t great, but they aren’t dreadful. However, I did visit Sintra at the tail end of September, so my view may not have been quite as optimistic if I'd visited in the height of summer! My advice to anyone visiting Sintra would be to get there early, and plan ahead!

After the steep and windy climb up to the entrance of the palace, there’s a final, relatively short ascent up to the palace itself. From the entrance you can walk up, or catch a small shuttle bus which runs back and forth. As a vocal critic of any kind of hill walking, I opted to catch the shuttle bus. If you choose to do the same, don’t make the same mistake as I did - you will need a token for this bus, which you have to buy in the palace shop, immediately on the right as you enter the gates! At least half of us in the queue made it to the front and attempted to board the bus before we were sent right back again! Or you could burn some calories and walk up to the palace in less time than I spent waiting, probably.

Pena Palace, Sintra
Pena Palace

Pena Palace

I’ve never been to Disneyland, but I’d probably consider it to be as obnoxious and gaudy as Pena Palace if I went. Pena Palace looks like something out of a fairytale, but one designed (and coloured in) by someone under the age of eight. I’m being critical, but I wasn’t as mesmerised and enthralled by the palace as perhaps it was intended. Fantastic for the photo ops, and I’m glad I can say I’ve been there, but I spent forty minutes in total at the palace - definitely less time than I spent getting there in the first place.

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Apart from the shuttle bus queuing debacle, I couldn’t have made it to Pena Palace much earlier, and it was already relatively busy when I arrived. An eye-watering queue already snaked halfway down to the main entrance which, after trying to work out what the queue was actually for, I found to be a queue for visiting the inside of the palace, which I wasn’t planning to see. (This same queue extended out of the palace’s entrance and down towards the road by the time I left - I have no idea how long it would have taken for it to dissipate, and I shudder to think how many people stood there and waited by mistake!)

As I said, I spent around forty minutes exploring the - relatively limited - exterior of the palace. It’s one to tick off the bucket list, but it’s not something I’ll be telling the grandkids about.

Pena Palace, Sintra
Pena Palace

Quinta da Regaleira

So, hang on, I’ve begun my “Lisbon highlights” post not only with a town that isn’t even in Lisbon, but one whose public transportation and main attraction I have complained about...did I, or did I not, enjoy Sintra?

Pena Palace wasn’t all it was cracked up to be, but that was only the start of my day in Sintra. I had hoped to visit both the Quinta da Regaleira and Monserrate Palace, but ended up only fitting in the first - it was this part of Sintra that takes the first spot on my highlights list!

To reach the quinta, I rode the 434 bus for the rest of its circular route back to Sintra station, where I changed to the 435 bus. This would take me directly to the quinta, passing the National Palace and Seteais Palace on the way (and would travel onwards to Monserrate Palace, if I’d had time!).

A quinta - as Wikipedia informs me - is the traditional term for an estate. Quintas are normally rural, and commonly include historic manors, as is the case with the Quinta da Regaleira, where The Palace of Monteiro the Millionaire is located. I don’t know much about architecture, but I do know that I love buildings that are gothic in style - if you too have a penchant for pinnacles and gargoyles, you’ll find the palace as stunning as I did!

Quinta da Regaleira, Sintra
Outside the Palace of Monteiro the Millionaire

It was the quinta’s park that I was most interested in, however, and didn’t actually venture into the palace or its chapel. The park felt like a grown up’s playground; within four hectares are towers, tunnels, wells, waterfalls, caves, and lakes, which certainly brought out the little kid in me! I spent forty minutes wandering around Pena Palace, and two-and-a-half hours exploring the park at the quinta!

Female travel blogger at the Quinta da Regaleira, Sintra
Exploring one of the many towers at the Quinta da Regaleira

You’ll have likely seen many of the structures in the park on Instagram if you follow other bloggers and travel-grams, but I’ll show you my top three:

  • The Initiation Wells: there are two wells in the park which take the form of “inverted towers”, lined with stairs from top to bottom, and they are known as the Initiation Wells for their use in Tarot initiation ceremonies! The second of the two wells is unfinished (not shown here), but takes a similar form. If you’re willing to climb down to the bottom of the well, you’ll find a tunnel that connects the two together! I didn’t get any typical ‘gram shots of myself posing in the well, but there’s a happy-looking lady in one of my photos who will suffice!

  • Tunnel from the Eastern Grotto: I’ve also seen this tunnel named the “Cave of the Orient”, and it connects the Eastern Grotto to the Unfinished Well and Waterfall Lake. This was one of the final elements of the park I came across as I specifically searched for the iconic Waterfall Lake!

  • Waterfall Lake: You can access Waterfall Lake from the path to which it sits adjacent, but if you’re looking to have a go at traversing the treacherous-looking stepping stones, you have to find your way into the cave first! My afternoon at the Quinta da Regaleira could be described as my quest to find Waterfall Lake, and it was so worth the time I spent searching!

(swipe through) The Initiation Well, Cave of the Orient, and Waterfall Lake

I’ll leave most of the park’s mysteries for you to discover yourself - that was the most fun part of visiting the quinta! Despite having no time left to visit Monserrate Palace (a STUNNING palace you have almost definitely seen on Instagram), I thoroughly enjoyed my day in Sintra, and I’m glad I still have reasons to go back! It would be great to spend a couple of days exploring the rest of the town and its attractions, as well as taking the bus even further to Cabo da Roca - the westernmost point of Europe!

Female travel blogger at Quinta da Regaleira, Sintra
Overlooking the Quinta da Regaleira

2) The Hills Tramcar Tour

My second highlight - very much within the city of Lisbon this time - was the Hills Tramcar Tour. The transport nerd in me always comes out when I visit a city or country with particularly quirky or iconic forms of transport. Double-decked trains in Europe? Can’t get enough. Japanese bullet trains? INCREDIBLE.

I purchased an all-in-one ticket for the yellowbustours (#notspon) hop on/off buses for my time in Lisbon, and I’ll be writing another post about why I chose to do so, and how I made it work best for me as a solo traveller. One of the benefits of this ticket was that it included use of the Hills Tramcar Tour, so I didn’t have to buy an extra ticket.

While I used the bus routes as intended, to hop on and off and visit different places, the tram for me was an attraction in itself (nerd alert!). The areas visited by the tram were also ones I had explored pretty extensively by the time I got round to the tour (not to mention exceedingly hilly!), so it was nice to take a seat and be chauffeured around the tiny, windy streets of some of Lisbon’s neighbourhoods!

Lisbon Hills Tramcar Tour
Enjoying having the tram to myself for a little while

Among the hundreds of photos I took while in Lisbon, apparently I managed to take zero photos of the trams, let alone the less-common red hills trams! I’ve included a couple of photos by far more talented photographers than myself (Annie Spratt and Etienne Gobeli), featuring both the yellow city trams and the red hills trams.

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The 90-minute tour takes you through some of the most iconic neighbourhoods in central Lisbon, such as Alfama - in which I was staying - and the Castelo area, Baixa, and Bairro Alto.

Lisbon’s Neighbourhoods

I joined the tour at the Praça do Comércio, the iconic square in the centre of Lisbon, overlooking the Tagus River. This is where you will find the Arco da Rua Augusta - the big arch on the north side of the square, from which you can enjoy amazing views over the Praça and beyond. I wish I hadn’t missed out on this! A number of tram routes make a stop here, including the Hills Tramcar.

The Praça lies in the centre of the Baixa region of Lisbon, which is characterised as being one of the flatter regions of the city, as well as the most elegant; this is where you’ll find the most expensive boutiques and establishments in the city.

Travelling on the Hills Tramcar - or around Lisbon in general - you will notice a significant juxtaposition between Baixa and the surrounding neighbourhoods. Baixa is formed of large and spacious plazas, boulevards and avenues, which is a stark contrast to many of the tightly interwoven streets found in the hillier areas of Lisbon, with buildings almost within arm’s reach of one another.

Praça dos Restauradores at sunrise - a perfect example of Pombaline design

A Quick History Lesson

It is the contrast in architecture and street layout that provides a clear and constant reminder of the 1755 Lisbon earthquake and its aftermath. This earthquake almost totally destroyed Lisbon, and is considered one of the deadliest in history. Following the earthquake, a tsunami - and two further waves - rushed up the Tagus River and inundated the city. The events coincided with All Saints’ Day, during which time candles were lit in the homes of those celebrating; the earthquakes and subsequent tsunamis caused many of these candles to fall, and Lisbon became engulfed by a firestorm which burned for hours. Between 10,000 and 100,000 people are believed to have died, and 85% of Lisbon’s buildings were destroyed.

Following the tragedy, the Marquis of Pombal - ruling over Portugal at the time - ordered for what was left of Baixa to be razed to the ground, and rebuilt with a new vision in mind. The Marquis felt that wide streets and large squares would be less susceptible to damage in the event of another earthquake or tsunami. New buildings, later termed to be “Pombaline” in style, were also among some of the earliest seismically-protected structures in Europe. The new Baixa was completed, and still portrays the Marquis’ vision today.

After Baixa, we twisted our way through the tiny streets of Alfama, one of the city’s oldest districts. This area of Lisbon - originally lying beyond the city walls - was previously associated with poverty and squalor, and residents were not afforded the luxury of space. Alfama is characterised by narrow cobbled streets lined by tall buildings of three or more storeys, and it is very hilly! The once poorly thought of neighbourhood now takes pride in its once-unfavourable traits - my Airbnb was right in the centre of Alfama, and I thought it was nothing short of charming! Buildings are brightly coloured, and many streets are too small for cars, making it a great place to explore and get lost. Alfama is also the district that lies immediately beneath the Castelo de São Jorge, which is another must-see in Lisbon!

Rua das Farinhas, Lisbon
Rua das Farinhas - my front door is just to the right of this photo!

I am most definitely a fan of irony, and I will not forget, as we wound our way around these tiny streets, the tram’s audio guide making mention of how car drivers in Lisbon are experts in knowing how and where to park, utilising space down to the last millimetre in order for the trams to fit past them. I’m pretty sure that, at that very same moment (and certainly on numerous occasions throughout the tour), our tram driver had his head out of the window of the vehicle in order to shout at a car driver who was in his way. This happened a lot during our trip, and it made me laugh every time.

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With Alfama on Baixa’s east, Bairro Alto lies to the west. This part of the city also used to exist outside of the city walls, this time as a result of urban expansion within Lisbon itself. Another hilly area of Lisbon, Bairro Alto follows a medieval layout of roads and perpendicular lanes, following an east-west and north-south alignment, although navigating the roads isn't quite as tricky as with those in Alfama. This is an area of Lisbon I didn’t get to spend too much time in, but what I did see was pretty. Bairro Alto apparently also boasts the best nightlife in the city, although I was tucked up in bed far too early to have experienced this myself!

I thoroughly enjoyed my ride on the Hills Tramcar tour, and would highly recommend it if you have a spare couple of hours, or you can use it to reach some of the attractions within Lisbon. If you’re anything of a transport nerd like myself, you definitely won’t want to miss it!

3) Jerónimos Monastery

I have saved my absolute favourite highlight for last - the Jerónimos Monastery in Belém!

The monastery was something I knew I had to see while in Lisbon, but I didn’t have it in my sights as something I would fall in love with. It actually took me two attempts to visit the monastery; both times I travelled to Belém with yellowbustours, as they stop at all the important attractions, of course including the monastery. The first time I reached Belém it must have already been mid-afternoon - everything was super busy, and there was a queue about half a mile long stretching from the ticket booth, so I ‘noped’ on the monastery and caught the next bus onto the Belém tower (which I also ‘noped’ on!).

The second time I visited Belém it was earlier in the day, just coming up to lunchtime. The area was already busy, but I decided I now had time to brave the queue and visit the monastery. I was anticipating maybe an hour’s wait to buy my ticket - an hour’s wait with no shade in the midday sun. Yippee.

The exterior of Jeronimos Monastery, Lisbon
I've had worse views from a queue

PRO TIP: I don’t know whether this is an official thing, but it worked for me on the day….take note of the second entrance into the monastery building, to the west of the main entrance. Unless there has been a big improvement to the signposting when you go, the big queue forms outside the ticket office at the easternmost entrance, closest to the town, BUT when I was there, there was no queue whatsoever outside the second entrance, which I believe we had all assumed was the entrance to the maritime museum next door. You can buy tickets to the monastery just inside this door. A few of us ditched the queue we had joined, bought our tickets from this second ticket office, and then bypassed the entire queue and went straight into the monastery! Definitely investigate whether this is the case on your visit!

Anyway, after I had gained about an hour of my day, I entered the monastery. You can buy tickets to other elements and rooms in the monastery, I believe, but your general admission tickets lets you see the main section, which includes two storeys overlooking a courtyard in the centre. It is beautiful. This building truly took my breath away.

Jeronimos Monastery, Lisbon
One of my favourite angles of the Jerónimos Monastery

Like I said, I’m not much of an archophile, but Wikipedia assures me that the monastery is “one of the most prominent examples of the Portuguese Late Gothic Manueline style of architecture in Lisbon”, and that it is a UNESCO World Heritage Site. Manueline architecture is typified by being incredibly ornate, and including maritime-themed sculptures. The maritime and naval themes relate to the role of the Hieronymite monks, who occupied the monastery, praying for spiritual assistance for the sailors who departed from the port of Restelo. The Hieronymite monks occupied the monastery from the 15th century until 1833, when the religious orders were dissolved and the monastery was abandoned.

Jeronimos Monastery, Lisbon
Jerónimos or Hogwarts?

As well as its gothic style, it was the detail and delicate-ness of the building that blew me away. There are countless arches and spires that appear to have been meticulously designed down to the last millimetre. While the exterior of the monastery appeared white in colour, the limestone around the courtyard seemed to glow golden, particularly in direct sunlight; the whole structure just looks magical.

Jeronimos Monastery, Lisbon
Overlooking the courtyard of the monastery

I didn’t think I would need to spend a lot of time in the monastery, but I definitely spent a good two hours walking around, taking some photos, and admiring the building and its courtyard from every angle. Despite the lengthy queue outside (or maybe as proof of it), it wasn’t very busy, and there were times when I had a whole section of the building to myself, if only for a minute or so.

Jeronimos Monastery, Lisbon
Gorgeous decorative arches along a length of the monastery

Although it was my favourite highlight, I feel like I have the least to say about the Jerónimos Monastery. While the pictures do not do justice to the building itself, I think I’ll have to let them do the talking.


I hope you enjoyed reading about my top three Lisbon highlights! Originally I wanted to include my top five, but we would have been here all day!

For more Lisbon content, check out my experience exploring Lisbon with Yellow Bus Tours!

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