I went to Portugal with one of my childhood friends that hadn't taken any PTO in 7 months and was aching to get out of the country. I was the only one able to join him, so we decided to do an easier trip in Portugal since we could go for a few days over MLK weekend and cover two cities considering the relatively shorter flight. We had a great time in Lisbon, and despite only having one adventure-filled day in Porto, it was still a great time. However, the weather we got for half our trip was foggy/rainy which made our day trips to Sintra and Porto a little less than ideal. Still, due to some beautiful natural views, great food, and lots of activities, I would still rank this as a very solid trip and would recommend for anyone looking to get out of the country for a long weekend.

BONUS: I ended up going back to Portugal during Valentine's weekend in 2026 with one of my other best friends. It was the first time we had both traveled together, and since we had both already seen Lisbon, it was a very relaxing and chill weekend. We ate good food, went out on Pink Street, and took it easy all weekend -- any locations with a star are from my second time in the city while the rest of the information is from the first trip since we didn't do much our second time around.

Day 1: Lisbon Day 1

• Take a Delta red eye from JFK Thursday night at 8 PM reaching Lisbon at 8 AM on Friday

• Head to the hotel and leave bags and grab a coffee to power through the jetlag for the first day

  • We stayed at the Meraprime Gold Hotel, which was a great hotel and would definitely recommend

• Walk around the streets of Lisbon and explore each of the below:

  • Arco da Rua Augusta --> landmark monument 

  • Praca do Comercio --> central square between the water and city

  • Santa Maria Maior --> small beach and pier right by the above square with a nice view of the other side of Portugal

  • Lisbon Cathedral --> pretty building, but we did not bother paying to be able to go inside

  • Sao Jorge Castle --> castle perched at the top of the hills of Lisbon with beautiful views of the entire city and coastline

• Take a break to go and eat lunch at Prado before heading back to the hotel to check in and unpack/rest for a few minutes

• Continue on to Elevador de Santa Justa 

  • There is a really long line to use the elevator itself; in our opinion, riding the elevator is not worth it and there is a quick walkaround method to get to the same view point that it gives you of the town of Baixa from above without waiting in it -- we used this guide

• Keep walking through the streets and seeing things like Praca dom Pedro IV, Carmo Convent ruins, and Praca Luis da Cameos

• About an hour before sunset, head to Miradouro da Senhora do Monte for one of the most gorgeous views you will see in your life

• Head back towards the hotel towards the street with all the restaurants and pick any of them to eat dinner at

  • Opt to sit outside so you can see performances passing by on the streets and enjoy all the people walking by

Day 2: Lisbon Day 2 + Cascais Half-Day Trip

• Head towards Time Out Market to eat breakfast and try the pastel de natas, which are a Portugal staple

  • On the way, we stopped by to see Pink Street, a stretch of bars and clubs where the tourists usually go out

• Head to the Belem side of town, and see each of the following:

  • The Church of Santa Maria --> beautiful church, free entry 

  • Jeronimos Monastery --> final resting place of Vasco de Gama, and a very cute building which is a must-see

  • The Monument to the Discoveries --> very cool monument right across the street from the monastery

    • Can see the "Golden Gate" Bridge from here as well

• Tower of Belem --> cool architectural fort, but had a really long line so we did not bother going inside

• Uber to the Parque de Eduardo VII, which is Lisbon's version of Central Park

• Walk through the park towards Selllva to eat lunch with some authentic Brazilian food

• Walk down the Av de Liberdade which is the street with all the luxurious stores and brands to shop at

• Take the path next to the Gloria Funicular up the incline to see another view of all of Lisbon and its famous red roofs

  • We ended up catching a live proposal up here which was really cool to see

• Uber to Cascais around 4 PM to catch the second half of the day in the beach town

  • Check out the piers with the Ferris wheel and all the people right by the beach

  • Walk along the coastline until you get to the Boca do Inferno

    • Make sure to go a little earlier in the day to see this since it's not exactly visible in the dark

• Eat dinner before heading back to Lisbon to go to a sports bar to watch the NFL playoffs

Day 3: Sintra Day Trip + Tasting Menu Dinner

• Uber to Sintra in the morning and head to Cafe Saudade before starting the Sintra exploration

  • The easiest way to explore Sintra is to buy the day pass for the Sintra bus which runs in a loop and you can treat it like a hop on/hop off type of bus

• Take the bus up to the first stop which is the Moorish Castle

  • This castle is a fun thing to walk through and see because of its interesting architecture and views of the Portugal wilderness

• After the Moorish castle, take the bus to the next stop, which is the highlight of Sintra: the Pena Palace

  • The palace is a very colorful building in great condition considering how old it is with authentic furniture and decorations inside to display how royalty used to live

• Take the bus back to the main part of Sintra and walk through the streets of the quaint town

  • We found a tile store where a man's son sold all of his father's hand made tile designs and ended up buying a few

  • We also stopped at a little wine bar to eat some food after all the moving around

• Head back to Lisbon to relax for a bit before a tasting menu dinner at Salta

  • This is one of the best tasting menu dinners I have ever had and the wine pairing is well worth the value considering they give a drink with all 8 courses in the menu

• Walk back to the hotel for an early night ahead of a very early morning

Day 4: Porto Day Trip

• Wake up early to take a 7 AM bus trip to Porto for a day trip which will reach at 10:30 AM

• When we got to Porto, I accidentally left my phone in the first Uber which was a fun adventure to get back without having any two-factor authentication ability and it ended up involving the Porto police department, but it ended up all being fine

• While we waited to see if anyone would return my phone, we got lunch at Do Norte Cafe which was one of the best breakfast plates I have ever eaten for a very cheap price

• Walk through the streets of Porto and see the following:

  • Clerigos Tower --> church in the middle of Porto that you can climb to the top of and see Porto's views

  • Livraria Lello --> the library that inspired the description of the libraries in Harry Potter; you end up getting a $10 off coupon with your purchase of the $10 ticket to enter so definitely buy a book

  • Majestic Cafe --> the coffee shop which JK Rowling sat in to write the Harry Potter books

  • Ponce de Leon Bridge --> beautiful bridge that you can stroll across while trams run by you and see the river running through the city

  • Stroll the Cais da Ribeira --> street right next to the river with lots of cafes, street performers, and cute vibes 

• There was a thrift market going on near this street that we popped into and ended up buying some clothes at, but it seemed to be seasonal

• Eat dinner at Muro do Bacalhau, a really good Portuguese restaurant on the Cais da Riberia before ubering back to the bus station to come back to Lisbon

​Day 5: Fly back to JFK!