In Love With Lisbon

by Dawn · Published September 25, 2025 · Updated January 6, 2026

Place: Europe

Country: Portugal

Towns/Cities: Lisbon, Sintra

Time of Year: August/September 2025

How we got there: Plane, Uber, Cable Car, Funicular

There are so many reasons to be in love with Lisbon, Portugal! Could it be the terracotta roofs spread on the hillsides, the trams and funiculars that carry you all over the city, the scrumbscious pastries on every corner, the ancient castles or the Moorish influenced architecture and tile work? I am thinking it is a little of everything! What better place to spend our 30th wedding anniversary and to make it even more special we brought along Cesar’s brother Alex and his wife Lisa!

Portugal has become a popular influencer hotspot making it a sought after vacation spot. Therefore, finding low cost plane tickets was not easy. In fact we spent more than I usually would to get us from Phoenix to Lisbon and this required a 5 hour layover in Montreal, Canada. We flew Canada Air for the very first time (meaning no status) however the flights were uneventful. Wish I could say that for the layover in Montreal!

Cesar and I have been to Montreal in the past and have fond memories of our visit, especially a unique visit to a particular Jewish deli. We wanted to share this experience with Alex and Lisa so, against my better judgment, we jumped in an Uber (had to wait in line 40 minutes to get one) and rode into the city (another 45 minutes) to Schwartz’s. We got right in thanks to the new outdoor street tent with tables. They didn’t have this on our first visit which made the seating arrangement the most unique part of our experience! Our lunch of smoked brisket, poutine and pickles was delicious!

By the time we finished eating, we had under 2 hours before our plane took off for Lisbon. We still had to drive back to the airport which would be 45 minutes, retrieve our luggage from the luggage storage (we never check luggage when traveling internationally) and go through TSA again. We picked up an Uber from a sidestreet and started back only to get rear ended!! My blood was boiling as we watched the driver yell at the young girl who hit us and all I could think was that we were going to miss that plane! In the end Cesar talked the driver off a ledge and he drove us back to the airport in the nick of time! Lesson learned; 5 hours is not enough time to venture into a large city on a layover but it does make for a good story we can laugh at now (not during)!

Our plane touched down in Lisbon at 8:30am and boy were we glad to have an electronic US passport! Customs was quick and easy for us but those without had extremely long lines and a few hours wait in front of them. Side note: we do have Global Entry which makes international travel so much easier. I highly recommend it! Our Chase credit card reimbursed us the cost and all we had to do was schedule a one time interview at the airport. Well worth it!

Before leaving the airport, we stopped in at the tourist kiosk to collect our “Lisboa Cards” which I purchased through Get Your Guide in advance. I booked all of our excursions through Get Your Guide and we were very happy with our experiences. Our Lisboa Cards allowed us to ride all public transportation such as trolleys, trams, funiculars, buses and the metro. It also covered admission to many of the Lisbon attractions we would be visiting. It was a great investment!

I had contacted our Airbnb host in advance to see if it would be possible to check in early due to our overnight flight. They were gracious enough to agree so we pick up an Uber and headed right over to get freshened up. A note here: Uber or Bolt car services in Lisbon are extremely cheap and easy to use . It cost 7 Euros for 4 people from the airport to our airbnb in Alfama. We opted not to use public transportation from the airport because we had luggage and wanted to get there fast! Also, the Lisboa Card works in terms of hours: 24, 48 or 72. We bought 72 hour passes and the time starts the first time you scan the card.

The Airbnb was named “In Love with Alfama” and I can truly say I was in love with this apartment! We had 5 tiny “balconies” overlooking Escolas Gerais which is a narrow street where the famous Tram 28 passes through every 11 minutes! There was a tram stop right outside our door which was convenient however the best part was watching the tram come and go from our balconies!

Day 1

Once freshened up, we headed out to explore! One rule we stick to is to not nap once we arrive after a long travel day! We must get on the local time right away! It is not as hard as it seems due to the excitement bubbling up inside to see the city! I had made a detailed itinerary for each day of our trip and we needed to start checking off boxes! There were a couple of “must see” view points in walking distance so we headed up the cobblestone street to find them! Lisbon is full of hills and cobblestones so wear the most comfortable walking shoes you have!

First stop Miradourodas Portas do Sol. This was our first view of the terracotta rooftops!

Next stop Miradourado de Santa Luzia

The Lisboa Card was activated for the first time when we visited Sao Jorge Castle. We did not have to wait in the long line to purchase tickets. There was a separate line for Lisboa Card holders to go straight to the front! Another perk of having the card! We learned a little history of the ancient castle but most of all we enjoyed the views over the city!

Praca do Comericco, Baixa & Arco de Rua Augusta were next on the list.

We checked out the Lisbon Cathedral and got a treat to combat the heat!

The last order for the day before climbing into our comfy beds for a well needed rest was to stop by the local grocery store to pick up some snacks and dinner options! This is one of my favorite things to do while traveling in a foreign country! It is so cool to see all the different products offered and taste new things! It is also far less expensive than eating out every night! I always bring a folded up grocery bag in my luggage to use while shopping.

Tram 28 took us right back to the front door of our building!

This is the night view from our balconies! Notice that the cobblestone road is only wide enough for 1 car or tram at a time. This is a two way street, so there are traffic lights at the end of the road letting cars know when the trolley is about to come through. You don’t want to be headed the wrong way when the trolley passes because there is no room to pull over!.

Day 2

Day 2 was packed with activities starting with our Pastel De Nata baking class. We rode Tram 28 then transferred to a bus and were dropped off right in front of the baking school called Homecooking Lisbon.

From scratch, we prepared the famous Pastel de Nata with instruction from our chef Miguel. This is a delicate process and so fascinating to see how the flakey layers are created. Very much like a croissant is made I’m guessing! This egg custard tart was so delicious right out of the oven and sprinkled with cinnamon! We got to taste our creations alongside the Portuguese sour cherry liqueur called Ginjinha(Ginja). The Ginja tasted a lot like cough syrup! What a fun experience and I have to say that they tasted way better homemade than the ones we bought at the store the night before! All the extras were packed in a box for us to take with us! This was an activity I booked on Get Your Guide and we all loved it!

Belem was our next place of interest and we hopped on the metro train to get there. The plan was to visit Belem Tower and Belem Monastery however the Belem Tower turned out to be closed and hidden behind scaffolding. That was a little disappointing since nothing in my research including google told us that it would be closed. We got a few pictures anyway.

One of the big attractions in Belem is the Jeronimos Monastery where we stopped to take pictures but opted not to go inside. This was included on our Lisboa Card FYI.

Instead we choose to visit the Monument to the Discoveries located directly in front of the monastery. I thought this monument was particularly beautiful. Our Lisboa Card got us to the front of the line and we rode an elevator to the top for a nice view of the water, Belem Tower and the monastery. There is also an interesting museum in the basement of the monument.

By this time we were pretty hungry and all we had eaten all day was our Pastel de Natas! I had heard that the LX Market was a good place to eat and walk around so we made our way over on the train. Most of the restaurants are touristy but the art and atmosphere were nice. We had Piri Piri chicken for lunch which was on my list of things to try! It was spicier than we expected!

I tend to notice restroom signs in other countries and I really loved these from LX Market!

The last activity for day 2 was a sunset sail on the Tagus River! This was a highlight for all of us! There is something peaceful about being out on the water at sunset drinking wine and viewing the sights of Lisbon. Christ the King was towering from the hill and the Ponte 25 de Abril suspension bridge floated above us. This city so much reminded me of San Francisco but never so much as when we were floating beneath this bridge!

The best part of all was when they let me drive the boat! And wear the hat! So much fun!!

Day 3

Visiting Sintra is a “must do” when in Portugal. The town of Sintra was a royal retreat tucked in the Sintra Mountains where the royals build castles, palaces and gardens much like you would see in fairytales. We definitely wanted to take a day trip to enjoy this UNESCO World Heritage Site. I’m usually not big on tour groups but in this case I am so glad we were part of a tour. Again, I used Get Your Guide to book our tickets. When researching I found that we could have used our Lisboa Card to take the train to Sintra and purchase castle entry tickets separately, but I am so relieved that I went with my gut and paid for the tour. Our tour included a 45 minute tour bus ride from Lisbon city center to Sintra with two guides, entry tickets to the castles/palaces and headphones to hear the tour.

The bus dropped us in the little town of Sintra to get breakfast and coffee before the tour started. Sintra is known for two pastries Travesseiros de Sintra (almond and egg cream) and Queijadas de Sintra (cheese tart) which we tried at a local pastry shop.

We could already tell that this place was going to be crowded! After breakfast, we walked up the steep hill to Quinta da Regaleira where we viewed the well and gardens of this wealthy retreat. Our guide shared the history and gave us time to wonder around the “over the top” gardens.

Then we toured the estate.

From here we hopped on a smaller tour bus because the larger one would not be able to climb the hill to our next stop! Up a winding narrow road on a hill in the Sintra Mountains right above the town of Sintra sits Pena Castle. This primary colored Romanticist palace is one of the 7 wonders of Portugal and you can probably see why from the pictures! We visited on a clear day however this castle is often covered in fog!

I have to say that there were hundreds of people at Pena Castle in the afternoon. This is why I was so happy to have booked the tour! We went straight in with no waiting( the line to get in was super long) and we got to hear more about the history of this incredible example of architecture.

The tile work was beautiful and I particularly liked the “sea monster” gracing the entrance with is coral, seashells and double mermaid legs!

After of palace and castle tours, the bus took us to Cabo da Roca for some coastal views before heading back to Lisbon through the high end town of Cascais where the rich and famous purchase homes and shop in luxury shops!

But our day was not over! Once back in the city square, we still had time to jump on the Justa Lift and once again we got to the front of the line with our Lisboa cards!

Hunger was setting in at this point so we found an Italian restaurant close by in the Baixa District where we ordered pizza (good but not as good as in Italy!) and tried the popular Aperol Spritz which happened to be the drink of the 2025 US Open that was going on in NY at the same time.

Day 4

On our 4th day in Lisbon, Cesar and I celebrated our 30th wedding anniversary! What better way to celebrate than to travel the world together! This would also be our last day before flying the the island of Madeira so we had to check off a few more of the “must do’s”.

We started the day at the little coffee shop across the street from our Airbnb like we did every morning. They had the most delicious breakfast sandwiches, overnight oats and pastries as well as coffee and tea. The outside is deceiving as it is just a door right off the narrow street but right inside down a flight of steps is the cutest indoor/outdoor eating area.

After breakfast, we walked through the streets of Alfama where we were staying and admired all the cute little alleyways with laundry waving in the breeze, then caught a bus to The National Tile Museum in the Xabregas neighborhood.

Again, we gained entry to the museum using our handy dandy Lisboa Card! We were gazing at all the tile displays when we were approached by a young university student giving free history tours and we jumped at the offer! She did quite a nice job explaining the history of the building that the tile museum was housed in. We had no idea that we were standing in the former Madre de Deus Convent! The stories of the convent were so fascinating!

After the museum we entered the metro station with our Lisboa cards and took the train to the Bica Neighborhood in search of the Bica Funicular!

The Bica Funicular was something I was very excited about! Like I mentioned before, Lisbon is very hilly and a lot like San Francisco. Funiculars are used to get up and down steep streets and are very popular for tourists and locals alike. I mean who wants to walk up and down those streets multiple times a day! Our Lisboa Card covered the 4 Euro each way trip on the Bica which connects Largo do Calhariz to Rua de São Paulo. First we rode from the top to the bottom. Funiculars work on a two car pulley system so as one car goes down, the other car passes going up.

Once down at the bottom, we walked over to the Timeout Market for lunch. This indoor market is a collection of chef owned restaurants each serving their own specialty. There is so much to choose from! We got a pork sandwich which was on our list of things to try and took our food outside to sit in the nearby park. It was much too crowded and hot inside!

Since we were so close, we walked over to Pink Street just to say we have been there!

We used our last swipe of the Lisboa Card on the ride back up in the Bica Funicular. We had reached our 72 hour limit!! There was one more funicular I wanted to see so we walked over to the Elevator da Gloria. We took a few pictures of the Gloria which has been running for over 100 years then decided to visit the Miradouro de São Pedro de Alcântara which sits right next to the funicular. The views over the city were glorious and the weather was perfect so we bought some drinks and stayed for a while. Wild parrots flew above us and we could see the Sao Jorge Castle on the hill.

After our respite on the terrace, we went back over to the Gloria but talked ourselves out of riding it due to the fact that our passes had run out. We decided to walk down the hill instead passing a building with a “brain” on it and stopped to take a picture.

Little did we know at the moment that we would miss a fatal crash by less than 24 hours. On September 3, 2025 (the day after our visit) the Elevator da Gloria’s cable broke sending it crashing into the building shown above killing 16 people. I cannot describe the feeling of knowing that you were standing on the crash site only the day before. I am deeply saddened for the victims involved and for the city of Lisbon.

Our walk continued until be found ourselves back in the Baixa District where I remember a gelato shop that I really wanted to try. We had passed by the night before but were too full to eat another thing so I was thrilled that we happened upon it again! They make the prettiest gelato I’ve ever seen and it was tasty as well!

Well that would wrap up our last day in Lisbon, although we would spend one more day at the end of our trip. The next morning, we caught a 1.5 hour flight to the island of Madeira off the coast or Portugal. You can read all about that part of the trip here: https://dawntillduskaz.com/mad-about-madeira/

In case you are interested in what a Portuguese apartment looks like on the inside: