It goes without saying that it would not be a trip to mainland Portugal if you do not spend some time in the capital city. Lisbon is a truly special city with a heart and soul, and I am happy to share a handful of the most iconic experiences I have had while visiting.
This is a medieval castle in the center of Lisbon. It has great viewpoints of the city and you might even see some peacocks walking around the grounds of the castle!
This is a cafe in Chiado, a lively neighborhood in Lisbon with tons of shops. One of Portugal's most famous authors, Fernando Pessoa would spend his time here. He composed works under a variety of pseudonyms, sometimes writing critiques of his own works as his alter-egos! This is a nice spot to take a break and people-watch during a day in Lisbon.
Livraria Bertrand is the world's oldest bookstore and has quite an extensive collection. They also have a large English section if you need something for the flight back to the US.
For all the fans of contemporary art, this is an impressive collection. It is in Belem near the monastery and Naval Museum, so you might be able to fit a few things in along with a museum visit. I personally enjoyed the constructivist art section!
LX Factory is a lively area on the outskirts of Lisbon where you can find a wide range of activities and a cool bookstore. This is great for an easy afternoon.
Back in the day, Portugal's navy was important. Here you can see all the naval developments that contributed to Portugal establishing the world's first and longest-lasting colonial empire.
For those who enjoy a good find, Feira da Ladra is an open-air flea market that occurs every Tuesday and Saturday, starting at 9 AM. Make sure to bring cash in case the vendor does not take your "multibanco" (what everyone calls card).
This is intended more for the younger people. Bairro Alto is one of the most popular neighborhoods where people go out for drinks at night- typically more than two. Don't worry, they have good public transportation here!
During the day, Pink Street is a small pedestrian street that is often used as an open-air art gallery, but at night it is one of Lisbon's most popular destinations with lots of noise and plenty of bars. People tend to stay out here late into the night and often until the early morning.
Santos is a neighborhood that was best known in the 18th century for the mansions of aristocrats, but today is known for its bars and clubs that attract a younger crowd. If you go during the day, you can visit the Museum of Ancient Art.
If you are not staying in Cascais already, then you should spend some time here. You can take a stroll down Rua Amarela, or if you come early enough you may see the president take his morning swims at the beach. There are some great restaurants and bars, and you can either take a short Uber or long walk to Praia do Guincho, or ride the train a short way to Estoril(this is also where the officers planned the Carnation Revolution) where you can see their famous casino and food and crafts fair FIARTIL that often has live music.
Praia do Guincho is a lovely beach and a great surf spot. It is also typically less crowded than the other Lisbon beaches. You can rent both a board and a wetsuit here if you would like to surf. Take care though as the swells can be big and the water is cold(this feels fantastic on a hot summer day)!
Boca do Inferno (Mouth of Hell) is a unique rock formation on the coastline near Cascais where waves occasionally crash violently against the rocks. There are some excellent seafood restaurants nearby, such as Mar do Inferno that I highly recommend.
Sintra is a fairytale-esque town about 30 minutes outside of Lisbon that was previously the site of the royal family's summer retreat. You can pick up a few travasseiros(puff pastries) near the town square and then visit Palacio de Pena and Castelo dos Mouros. If you desire, you may end the day with a breathtaking view at the Moinho de Dom Quixote Bar overlooking the ocean.
This palace in Sintra is an interesting mix of architectural styles that primarily reflects the mysticism of its former owner Carvalho Monteiro who purchased the estate in 1892. The palace and grounds feature a Romanticist style that mixes Gothic, Roman, and Renaissance architecture.
Palacio de Pena is a magnificent 18th century Romanticist palace in Sintra, about 30 minutes outside of Lisbon. It has a wonderful view and definitely merits a visit if you have a day to spend in Sintra.
O Castelo dos Mouros is a fortress built by the Moors in the 8th and 9th century while Lisbon was still Al-Ushbuna, a province of the Gharb Al-Andalus. You should certainly pay a visit if you plan a day trip to Sintra
Moinho Dom Quixote is a bar in Sintra with a fantastic view and great drinks. It would be a great idea to finish your day trip in Sintra here watching the sunset while sipping a Caipirinha.
If you have a few extra days, we would definitely recommend taking a trip up to Porto. It is a beautiful and unique city that played a crucial role in the emergence of Portugal.
We visited on our last day in Porto and only blocked out part of the day, thinking this would only be about wines. We were surprised that there are several museums with one focusing on the history of Porto as the cradle of Portugal. You could definitely spend an entire day here visiting all the museums, and it is a lovely site with plenty of food and wine options.