Welcome to Portugal, the western little old rectangle of Europe. Full of history, beautiful monuments and castles, good food (better wine), awesome beaches and much more. The good news is that the country itself is small, and the main cities and points of interest are near each other.
First in the tour, the capital Lisbon of course. I suggest to start with a walk, a walk 1000 years back in time, when the Arabs ruled the city. Explore the very old and very narrow and steep streets and stairs of Alfama the oldest neighborhood of town.
Take your time (and take many photos) to go all the way up to St. Jorge castle. On the way up or down, route yourself to Miradouro de Santa Luzia for breathtaking sights, and to Sé Catedral the oldest church in town, and just 50 meters ahead? Another church! St. Anthony church marks the birthplace of the famous matchmaker saint, and he is always there (well his spirit anyway) just to help with every love problem of yours.
Leaving the old town follow the natural city expansion to downtown, this is the part of the city that was rebuilt after the 1755 earthquake, with straight and square streets, open spaces with lots of light, and beautiful architecture.
To give you a power boost, start in Rossio square just like a local drinking a shot of cherry liqueur called ginginha in the very small, yet historic, open-fronted bar A Ginginha. Just in front there is a small monument with the star of David, a tribute (and reminder) to the hundreds of people killed by the inquisition bonfire in the Lisbon massacre.
Take Rua Augusta and enjoy the walk to Praça do Comércio square, one of the big beautiful squares of Europe framed by the Tagus river, the bridge, and the boats. Proceed with the river on your left to Cais do Sodré, a place full of bars and restaurants ready to satisfy your famine and thirst. You should check out Pensao Amor an old brothel converterted into a fancy bar that actually kept some charm.
Beware, Cais do Sodré is just one of those places lost to gentrification. Pink street has too many tourists, few locals. Lots of bars and restaurants with little to no soul. High prices alert!
Time to move up to Chiado the posh neighborhood and the adjacent Bairro Alto the classic nightlife quarter. In Chiado please do take a coffee at A Brasileira with Fernando Pessoa (a famous dead poet) or if it’s the end of the day a drink (and a haircut) at O Purista. Do some shopping, the finest shops in town are in Chiado (and also in Avenida da Liberdade), checkout Livraria Bertrand, the oldest book store in the world, selling knowledge stamped on dead trees since 1732!
Bairro Alto comes alive at night, packed with restaurants, bars and people happily roaming the streets. Close to S. Pedro de Alcantara viewpoint I strongly suggest a drink in Pavilhão Chinês, one of the most beautiful bars in Lisbon. Also in Bairro Alto you will find Tasca do Chico, one of the last strongholds of bummer fado music. You can come in sit down have a glass of red wine and enjoy. Also a very good option to seat down, have a drink, and listen to fado, is Mesa de Frades in Alfama.
Fado nowadays is mostly served in an expensive tourist package sold by the hotels that includes the transportation, fado museum, fine dinner (this and that), and fado presentations. I’m pretty sure that you will eat good and enjoy your time if you choose this option but the bummer fado is way cheaper and perhaps more authentic.
Back to daytime you should visit Belém, still Lisbon just a bit off the city center, this is the district that best symbolizes the portuguese age of exploration and discovery. Easily reachable by train from Cais do Sodré heading to Cascais (just a couple of stops between), there you will find the iconic Belém Tower, a fortification dating back to the fifteen hundreds, the Jerónimos monastery dating back to the sixteen hundreds, also Padrão dos Descobrimentos a beautiful monument dating back to 1960 dedicated to prince Henry the navigator and the portuguese that discovered the roads of the sea. And of course, for me the main highlight of Belém, and the reason of all the work and hassle of sending boats filled with men across the globe, the Pastéis de Belém factory.
Please do the day trip do Sintra, Cabo da Roca and Cascais.
If you never went to a huge aquarium, consider going to Oceanário de Lisboa.
Do the 28 tram. Buy the tickets before in the subway (much cheaper), attention with the wallet (some pickpockets work in 28 tram).
Verde Minho – honest old fashion portuguese food. In the center of Lisbon and great prices.
Novo Edmundo – grilled meat and typical food. Outside the center, good price quality quantity relation.
Tasca da Esquina – portuguese fine dining. Expensive. In a place of the city with little to no touristic interest.
Cervejaria Trindade – in Chiado, old monastery (different and beautiful architecture for a restaurant). Good steaks and “pregos”. Not cheap nor very expensive.
Cervejaria Ramiro – if you are into seafood this is the place to be. Lots of tourists and queueing. Expensive to very expensive (varies a lot with the food you order). Going north by the ocean coast there are several restaurants with great seafood and much better prices.