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 steep streets 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 by the river to Cais do Sodré, a place full of bars and restaurants ready to satisfy your famine and thirst. You probably should check out Pensao Amor an old brothel converterted into a fancy bar that kept some charm.
Beware, Cais do Sodré is just one of those places lost to gentrification. Many tourists, few locals. Lots of bars and restaurants with little to no soul.
Time to move up to Chiado and Bairro Alto. Please do take a coffee at 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, checkout Livraria Bertrand, the oldest book store in the world, selling knowledge stamped on dead trees since 1732!
Bairro Alto, close to S. Pedro de Alcantara viewpoint I strongly suggest a drink in Pavilhão Chinês, one of the most beautiful bars in Lisbon, but much more important you should go to Tasca do Chico to ear fado. It’s one of the last, or probably the last underground true fado experience, that you sit down have a glass of red and enjoy. The other fado’s places that I know you must buy the tourist package (includes dinner, transportation, this and that) for 50 euros plus….
Don’t forget Belem.
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.