Lisbon, Cascais & Sintra in September as a Business Traveler

I am visiting Lisbon for the second time after 10 years, I remember eating a pastel de nata near the famous bridge that looks like Golden Gate bridge but isn’t! Back then I came for a conference and this time around it is also a business trip, so time is scarce, and I am trying to make the best of the limited time that I have!

Lisbon from the top

Practical Tips

Flight tickets: look for good tickets on Kiwi or WayAway platforms!

Hotel: You can find hotels suitable for your budget on Booking or Agoda.

Getting around: I used Uber and metro, if you are planning to rent a car, consider Rentalcars.

Tours: short on time and don’t want to spend any time planning? Choose GetYourGuide for the best local guides to show you around!

25 th April bridge in Lisbon

Arriving to Lisbon

The plane lands in the sunny Lisbon airport at the start of September. It is +28 degrees Celsius here and it truly feels like summer, so don’t forget to pack sunscreen!

I start by trying to figure out where the Uber pick up point is, after wandering for 15 minutes I still can’t pinpoint the exact location (turns it, it was a different level!), but, luckily, my driver calls me right after I order the car and manages to find me himself.

Since I have some business to do, I am staying outside the city center, near the office building, so I have a dilemma – should I drive back to the city center, in rush hour, or go elsewhere? I opt for Cascais, as there is store that I want to visit.

Are you looking for more ideas on what to do in Lisbon? Check out this 3 day Lisbon itinerary!


I drop my bags at the hotel and call another Uber (turns out to be the same one that just dropped me off!) and head to Cascais. Unfortunately, the store that I wanted to visit doesn’t have the product that I am looking to buy, so head out in the direction of the Citadel. The small streets are pretty, but the closer I come to water, the nastier the smell gets. Either the heat or problems with garbage disposal, but I see a lot of trash on the street and the impression isn’t great. Some shady types are wondering around (though my Portuguese friends say Cascais is very safe). I arrive to the beach, but no one is swimming, but a few people are playing volleyball or partying.

Sightseeing in Cascais

As most of the indoor activities are closed for the day, I decide to walk around and at least see the buildings from the outside. I arrive at the Citadel, built between 15th and 17th centuries. It used to serve as the fortress against pirate attacks. There is a beautiful marina right next to it. Finally, there aren’t that many people around anymore and I am feeling much more comfortable.

places to see in Cascais

As I continue walking, I see the Santa Maria lighthouse and at last I am truly amazed at the beauty of something here! When I approach the waterside, it is a low tide and I see cliffs uncovered by the receding water and the lighthouse shining in the distance. Truly a marvelous sight!

Santa Maria lighthouse in Cascais

I don’t stay long, as there is only an hour remaining til the sunset. I increase my walking pace and soon I am at the Boca Inferno – an archlike structure in the cliffs.Though I am more amazed at the waves crashing against the cliffs. I see signs all around warning of the dangers of the waves, but other visitors ignore the signs and freely wander around, even climbing over railings to take a better picture. Later I read that unfortunately quite a few people have been washed over the side.

I briskly walk by a man feeding a cat and bunch of seagulls disapprovingly looking at the sight, and try to get an Uber to reach the final location of the day. Unfortunately, none of the cars would accept my ride, it seems I am too far away from the tourist trails. My ride isn’t supposed to be long, and the price would have only been 6 euros, but everyone who accepts, isn’t even moving ahead. I stare at my phone for 15 minutes at one of the drivers having accepted my ride and haven’t moved away from the location, finally having to cancel. I try multiple apps and in the end my ride ends up being twice the original price and I reach Farol Do Cabo Rasa lighthouse exactly five minutes after the sunset.

Still, the sight is amazing. The waves are even more impressive and there are multiple other people enjoying the view. I see Cabo De Roca lighthouse in the distance, the Westernmost point of the continental Europe. The only worry is that it is rapidly getting dark, I am in the middle of nowhere and not sure if I will be able to get a car back. At least there are streetlights on this road! Surprisingly, I get a car right away, and four minutes later I am comfortably sitting in a car with a driver called Jefferson.

As I sit down, I notice a pair of sunglasses on the back seat and so we stop with the driver on the way to drop those off to the previous rider. This way I get to learn a bit more of the behind the scenes of lost & found in an Uber. The driver is talkative and when I mention having waited a long time before, he answers that most likely it is due to the football game that took place earlier, all the drivers must have been watching that! He also shares his stories of other items found on the backseat, such as wallets, and his summer in Algarve where aren’t that many Uber drivers so it is an excellent way to make more money. Driving an Uber is his occupation, and for his wife too, they drive this same car in shifts – he works afternoons til 1 am, she takes the morning shift. When we have nearly reached the hotel, he finally mentions regretting not moving to Guernsey island some years ago that would have offered a better life for his little daughter. But his wife refuses to leave Portugal. He says that one needs to work a lot and very hard to make ends meet around here. As we arrive at my hotel, I wish him luck and finally go to take some rest.

Tuk-tuk Tour in Lisbon

I wake up early, it must be not more than 5am, when AC really has become too loud to sleep. I open the window to let in some fresh air and after an hour wake up again – this time from a beautiful bird song. I also hear pigeons. All the sounds together make me feel like in an exotic movie.

I spend a long day at work, but, luckily, there is a chance to do a tuk-tuk tour in Lisbon! You can book one on the GetYourGuide platform)! This time around I really go down the memory lane, recognizing small streets and churches from all those years ago.

tuk tuk tour in Lisbon

The tour is fast paced, we stop in a couple of times to observe something, but we don’t leave the tuk tuk, so all views from the seat. There is a final stopping point at the city view point, where you can see the entire city at your feet! Pack a jacket, as that is one windy place!

At the end of the tour every person gets a still warm pastel de nata and soon we are on the road again, this time, going on the bigger roads and much faster, so I really get cold. The warm day leads to a chilly evening!

I am having dinner near the 25th of April bridge, so similar to it’s famous brother in San Francisco! I remember how seeing this bridge for the first time, I was only dreaming of seeing the Golden Gate bridge, but since I have been there twice, and now is the time for a repeat visit to Lisbon!

best places dor dining in lisbon

A Little Bit of Sintra

When I have mu next free evening, I am torn – where should I run, where should I go? The time is limited. Should I try Sintra now, or should I go there on the day of my flight? I decide to go right away, to be closer to the airport on the day of the departure. I would really like to see , Quinta da Regaleira and the initiation well, but unfortunately, it closes much earlier than I can get to it after work. Still, I want to use the chance to see at least Pena palace garden, if not the inside, and take an Uber there.

I again get a very talkative driver, her name is Maria. In the 40 minutes together she shares all of her romantic life stories and those are some stories! Falling in love with a man, how doesn’t love her back, but happens to have a twin, who is interested in her? What a twist!

We say goodbyes and I enter the palace grounds at the very last moment, and guards tell me that the closing time is in one hour. The ticket isn’t cheap, but I’d rather see something than nothing!

exploring pena palace gardne after hours

I ask the guards what should I focus on in the limited time that I have, and head off! I climb up the 14% hill, check out the palace from the outside and then venture into what looks like a magic forest, with trees and shrubs so green all around! The level of moisture is so high here that soon even my hair starts looking a bit curly!

cruz alta view point

The garden is spectacular, I want to stop at every tree and bench, as the nature is just breathtaking! Since there aren’t any new visitors arriving to the palace, most of the time I am alone here. Soon I reach Cruz Alta, the highest place in the Sintra mountains and observe the view all around. Again, I don’t have too much time remaining tils sunset. The weather isn’t the best – the sky is covered in thick clouds, so I am not hopeful for any good views, but I want to give it a try. On the way back I stop at a little house in the garden for a few pictures and then go to check if the staff was right about “good luck if you miss the closing time!” Of course, they let you out, and I am not the only one who has stayed a bit longer.

Getting my ride from here is difficult. Uber doesn’t come here for pick ups, so I use another app. Luckily, driver Bruno accepts right away and soon we are on the way. 30 minutes pass by on little windy roads and I get a small glimpse of what is Sintra about. When I reach Cabo do Roca, I am there… exactly five minutes after the sunset!

cabo do roca viewpoint sintra

The sky is completely gray, so I haven’t missed anything. It still looks magical around, though nothing like some of the pictures I have seen from sunny days. Yet, there is some beauty to the cliffs, especially, their pointy shapes, and the blinking of the lighthouse near me. I would love to go down to the Ursa beach! Another time, then.

When I was leaving Bruno’s car, he warned me that there isn’t any transport after 10pm. I laugh and say that I am not planning to stay that long, a 15 minute stay and I’ll be going back. Later I see Bruno smoking in the parking lot. Waiting for customers? For me? Indeed, I end up being the next rider and now drive to the hotel with him. Unfortunately, his English is very bad, so we don’t get a chance to chat.

Walking in the Center of Lisbon

The last day of my journey has arrived, and again I am mapping my plans of the day. Where should I leave my bag? I don’t feel like dragging it along for the entire day. I ask at the hotel and they recommend leaving it at the airport luggage storage! From there, the city is just a short metro ride away.

I leave the bag at the storage box outside the departures floor, pay 2 euros for the metro ticket and as I emerge on the other side, I receive a message that my flight has been delayed. One hour. Unfortunately, I am still required to show up at the original time. I am definitely not excited about this, as this means more time waiting at the airport that I could have spent in the city!

sightseeing in lisbon center

I start my walk with the Praça do Comércio. It is an incredibly sunny day, and I remember something a Portuguese friend had said – the one thing they love about Lisbon is the light in the city.

As I am walking in the square, I see this truly is the central tourist place. Where you have tourists, you have sunglasses salesmen. I am later told you can also buy all other sorts of things from them to see the world in color. I don’t get any unusual offers, and, since I am wearing sunglasses, I am not offered any by the salesmen.

trams in Lisbon

As I finish the tour of this place, I follow the tram tracks. The tram has been around since the 19th century. I turn to take a peek at the Santa Justa elevator that took people from one level of the city to the other. For me this is a new place, as I don’t remember seeing it the last time.

I turn around the corner to Santini and eat an enormous serving of mango orange ice cream before figuring out what to do next.

I decide to see a few more places to do with trams, and looking at the pictures I feel like I have been to one of these before. So I keep walking until I am suddenly in the place and indeed, I remember this place! I stay for quite some time, trying to take pictures without other people, but I don’t succeed. It is always packed!

tram in lisbon

Then I head to the famous Time Out Market, since it is lunchtime, the place is packed and somehow I don’t feel inspired about what I see here and I leave. And it is a good thing I do! As I am passing the street, I notice a place called Pastéis de Bacalhau, where one can eat cod pies with cheese! The smell of cheese is as strong as it gets, but after the first bite I understand why it has been added and the taste indeed is really very good!

Soon I cross Praça do Comércio again, stopping by a pancake place. I was thinking of eating here, but now I don’t feel hungy and decide to continue walking ahead. I get a bit worried about my flight, as online it is showing even more delayed. But I still have time, so I climb to the cathedral, passing by several view points. As I pass by the gates of the sun, I am amazed at the number of people here. It really didn’t used to be this full last time I visited! Is it because of the cruise ships? I also notice something I didn’t see before – way too many homeless people. My Portuguese friends tell me it has always been a problem, and that estimates put the number of homeless at around 5000.

instagrammable streets of lisbon

I continue on the same route as I did with tuk tuk, stopping by the oldest house in Lisbon. As I am there, I get another message from the airline – 30 more minutes delayed, but I am still expected to show up at the original time! That means I need to start heading in the direction of the airport. I find the nearest metro station on the map, Martim Moniz, and head in its direction. I manage to turn wrong somewhere and see both amazing places and places that don’t make me feel amazing about a wrong turn.

Finally, I emerge at the square and try to find the entrance to the metro. It is just pigeons, me and homeless people. As I find the metro entrance I notice two young men, seemingly without an aim, wandering on the stairs. One in front, one at the back. That just instinctively makes me feel something isn’t right and I pull my bag closer to me. Later I hear a story from an acquaintance that guys like that pulled out the phone and wallet from their hands exactly here!

using metro in lisbon

In Conclusion

After twenty minutes I am at the airport and there is plenty of time til my flight. I head to the business lounge to have a quick snack and start working on this travel story while the memories are fresh. When looking back at my short visit, I think about how good this trip has been. The food in Lisbon is great! The views in Sintra even more so! And I will always remember the comment of my friend saying they love light in Lisbon the most. Until the next time in Lisbon!

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