Lisbon – Long Weekend

Overview
In August 2015 I found myself with several unused vacation days and more than my fair share of free, almost-expired, Starwood Preferred Guest (SPG) nights. Given my ever-present wanderlust (which seems to only get worse and worse), those two reasons were more than enough for me to set my sights on taking an extended long weekend trip. Initially, I considered traveling to the Caribbean because of the relatively short and inexpensive flights from the east coast and because I never take relaxing vacations. However, given that it was hurricane season, I instead decided on Europe, specifically Portugal. It had been high on my travel list ever since I chose not to study abroad there in high school (instead opting for Italy). Timing could not have been more perfect as one of my closest friends, who was traveling around the world for nine months, was going to be in Portugal the weekend in September I planned to go. So I booked my flights, packed my bag and headed to beautiful Lisboa.
The entire trip was 5 days, with 3.5 in Lisbon and a bonus overnight layover in Madrid. In Lisbon we spent time exploring the city and squeezed in a day trip to Portugal’s west coast and the castles of Sintra. Before heading back to the U.S. I got a small taste of Madrid, which of course only left me wanting more.
Itinerary
Day 1 - Overnight flight to Lisbon (via Barcelona)
Day 2 - Exploring Lisbon
- Parque Eduardo VII
Day 3 - Exploring Lisbon
- Castelo de São Jorge
Day 4 - Day Trip to Cascais and Sintra
- Cascais
- Cabo da Roca (westernmost point on continental Europe)
- Palacio da Pena (Sintra)
Day 5 - Flight Lisbon to Madrid
- Belém
Day 6 - Morning Tour of Madrid and Flight Back
- Plaza Mayor
- Chocolateria de San Gines
Lodging
- Sheraton Lisboa: A beautiful, modern hotel with great views of Lisbon. It’s part of Starwood hotels. It’s about a 35 minute walk to the old part of Lisbon. Moderately priced.
- AirBnB: Has a lot of great options all over Lisbon. You can find a very conveniently located place for a great price.
- Westin Palace Madrid: An iconic, classy hotel located in the center of Madrid. It’s part of Starwood hotels. It’s within walking distance of many sites in the city. Moderately priced.
Detailed Itinerary/Sights
DAY 2: LISBON
After 10+ hours of travel and relatively no sleep (I still have not mastered the art of sleeping on planes despite countless hours in the air), I arrived at the Lisbon airport (LIS) at 11:30 AM. After getting off the plane, I headed to the metro to take the train downtown to the hotel. I spent a few minutes reveling in the sunshine on the short walk outside to the station, which is right by the arrivals area of the airport. I bought a metro card from the self-serving kiosks (around 1.50€ one way) and then hopped on the red line toward S. Sebastiao, getting off at the Saldanha stop (the Picoas stop on the yellow line was closer to the hotel, but I opted to walk a little farther to avoid switching lines). On the metro I met a Canadian man who was in Portugal with friends to hike from Lisbon down to the Algarve coast (mental note to add that to my list of future travels). I took the “scenic route” from the metro stop to the hotel (after wandering the wrong way from the metro exit) and arrived at the hotel around 1 PM.
I met my friend there and after freshening up and exploring the hotel, we grabbed lunch nearby at a place that served burgers and pizza (nothing to write home about). After eating we walked to Parque Eduardo VII, which is a beautiful, manicured park that overlooks downtown Lisbon and the water. We spent an hour relaxing, walking around and watching a group of high schoolers try to shoot a movie.

Parque Eduardo VII
Bairro Alto
In the early evening we walked 35 minutes from the hotel to Bairro Alto (which is a quaint neighborhood with a lot of bars and restaurants), in the old part of Lisbon. Since the weather is beautiful in September there were plenty of options for outdoor dining. We decided on a tapas place where we were seated at a table in the middle of the street (it averaged around 20€ per person including wine). While enjoying delicious Portuguese food, we were serenaded by musicians playing in the street nearby. After dinner we went to a nearby gelateria (because who can say no to gelato) and wandered into a used book store, Livraria Sa’ da Costa (on the corner of R. Garrett and R. Serpa Pinto) before heading down to Praça do Comércio by the water. We spent 15 minutes walking around there and sitting by the water.
DAY 3: LISBON
We checked out of our hotel in the morning and headed back down to the Bairro Alto area to check into our AirBnB, where we were staying for the next two nights. It was on this 35 minute hike with backpacks and suitcases that we truly understood what a hilly city Lisbon is. After a hot and sweaty trek, we finally made it to our AirBnB, which was much more conveniently located (just a few blocks from a ton of bars and restaurants).
Castelo de São Jorge
After eating lunch close to our AirBnB, we headed up to Castelo de São Jorge (8.5€ admission). On the way we walked up many more hills and passed by the Elevador de Santa Justa, which was built by the architect who designed the Eiffel Tour. You can take the elevator to the top for good views of the city (although it is recommended to go early or during off times), however, we opted to continue our trek to the castelo (which took around 30 minutes). Once we arrived at the castle (after wandering through some beautiful cobblestone streets), we walked along the wall and enjoyed the sunshine and beautiful views for 1.5-2 hours. We slowly meandered back down to our AirBnB and then once again chose someplace with outdoor seating for dinner.

View of Lisbon from Castelo de São Jorge
DAY 4: DAY TRIP
Cascais
Today we decided to wander outside of Lisbon for the day. We walked about 15-20 minutes to the Cais do Sodré train station where we caught the train to Cascais, a small town on the ocean. The train was very easy to use and we bought our tickets at the kiosks right at the station (2.15€ one way). It took 40 minutes to get to Cascais from Lisbon. Once there we wandered around the cute, cobblestone town and walked along the beach before eating at a delicious Italian restaurant (Cappriccio) overlooking the beach.

Hanging out at a beach in Caiscais
Cabo da Roca
After lunch we hopped on bus 403 to head to Cabo da Roca, the western most point in continental Europe (it was a 25 minute ride). The bus company was very easy to find in Cascais, a block away from the train station). We spent 30 minutes walking along the cliffs at Cabo da Roca and taking pictures (warning: don’t wear a skirt - it is very windy).

Cabo da Roca
Sintra
After walking along the cliffs and taking our pictures, we waited for the next bus (again bus 403) and then had a 35 minute ride to Sintra, where there are several beautiful castles. Since it was the late afternoon we decided to only go to the Palacio da Pena, which is a very colorful castle up on a hill. Once there you can purchase a ticket to go inside (14€). We decided to go into the castle, but didn’t spend too much time inside due to the influx of tourists. We instead spent more time walking around the outside and looking at the views of the surrounding hills. After spending an hour wandering around we took the bus back down to Sintra and then took the 30-40 minute train ride (2.15€) from there to the Rossio train station in Lisbon.

Palacio da Pena
DAY 5: LISBON TO MADRID
Belém
My flight out of Lisbon didn’t leave until 9 PM, so I had a partial day in Lisbon once my friend left early in the morning. I walked to the Cais do Sodré train station to take the 15 minute train to Belém, where there is a famous pastry shop, Pastéis de Belém. I went early in the morning to avoid the long lines later in the day; it was a 10 minute walk from the train station. Pastéis de Belém is famous for their pastel da nata, an egg tart pastry typical of Portugal, which was delicious! I then walked around Belém and made my way over to Padrão dos Descobrimentos and Torre de Belém, two famous landmarks there. After enjoying some down time, I took the train back to the AirBnB and checked out.

Pastel da nata from Pastéis de Belém
Travel
Since I did not want to tackle the Lisbon hills with my suitcase (now several pounds heavier due to the Portuguese wine I was bringing back for a friend), I headed to the airport early to await my flight to Madrid. I arrived in Madrid around midnight and checked into the Westin Palace Madrid. I was lucky enough to get upgraded and was put in a large room in their wing that had just been renovated a week earlier. Needless to say, it was beautiful.
DAY 6: MORNING IN MADRID AND FLIGHT BACK TO PHILADELPHIA
My flight back to Philadelphia left at 1 PM so I woke up early to explore Madrid for two hours before heading to the airport. I spent most of that time walking around and exploring random streets. I walked 10 minutes to Plaza Mayor on my way to Chocolatería San Gines for a breakfast of champions, churros and chocolate. I then walked another 10 minutes to Palacio Real before heading back in the direction of the hotel. I can’t say I saw even a fraction of Madrid but I definitely want to come back to see more. After an uneventful flight, I made it back to Philadelphia and straight back to work.
Churros and chocolate at San Gines in Madrid
- Parque Eduardo VII in Lisbon, Portugal
- Elevador de Santa Justa in Lisbon, Portugal
- View of Lisbon from Castelo de São Jorge
- View of Lisbon from Castelo de São Jorge
- View of Lisbon from Castelo de São Jorge
- Lisbon, Portugal
- Wandering the Streets in Cascais, Portugal
- Wandering the Streets in Cascais, Portugal
- Cabo da Roca, Portugal
- Cabo da Roca, Portugal
- Palacio da Pena in Sintra, Portugal
- Palacio da Pena in Sintra, Portugal
- Palacio da Pena in Sintra, Portugal
- Palacio da Pena in Sintra, Portugal
- Pastéis de Belém, Portugal
- Pastel de Nata from Pastéis de Belém
- Torre de Belém, Portugal
- Torre de Belém, Portugal
- Padrão dos Descobrimentos in Belém, Portugal
- Plaza Mayor in Madrid, Spain
- Plaza Mayor in Madrid, Spain
- Churros and chocolate at San Gines in Madrid, Spain