A compact city with plentiful golden sunshine and a reputation for cheap prices, Lisbon is more than just one of Europe’s most travel-friendly capitals. The city is also small enough for the determined traveler to tackle inside of 48 hours, although doing so might run afoul of the population’s relaxed ways and the sleepy atmosphere of what was once the center of the world’s greatest maritime empire. However, these are the qualities that give Lisbon its character, which is both energetic and deeply traditional at the same time, and make it a stellar destination for a weekend getaway.
After breakfast, make your way to Chiado Metro Station, and from there, transfer to the Number 28 Tram. Lisbon’s antique yellow tram cars are the stuff of travel guides and major motion pictures, so don’t miss the chance to ride one and enjoy the views while avoiding walking up steep hills. Dismount below the Castle of St. George (if confused, ask the tram driver “Castelo? Castelo?”) and start your walking tour.
Start by checking out the Castle of St. George and enjoying its commanding views of downtown Lisbon’s red tile roofs and clear blue skies. Then, move on to explore the narrow alleyways of the old Arab quarter, Alfama, before making your way back towards the center of Lisbon. On your way, be sure to walk past and visit the Se, Lisbon’s oldest cathedral and one of the few medieval buildings left in the city (the rest were destroyed in the great earthquake of 1755).
After a morning of sightseeing at the Castelo and Alfama, stop for a late lunch at Estrela da Se, a small restaurant less than half a block down the street from the namesake cathedral. This place is a preserved slice of 1920s Lisbon, and while a little cramped, the restaurant is thoroughly atmospheric. Try the bacalhau a bras, one of Portugal’s famous cod dishes, although the portion is big enough for two appetites.
Continue making your way downhill to see the squares of Lisbon’s Baixa and Rossio districts. Start with Praca Do Comercio on the riverfront, then move through the pedestrian shopping malls of Baixa to the Elevador de Santa Justa, an eccentric 10-story elevator tower reminiscent of the Eiffel Tower. Continue on into Praca da Figuerira and the Rossio.
If you have arrived here before about 4 p.m., you might check out the Convento do Carmo or an exhibition at Rossio Train Station, both of which are nearby, or simply people-watch. However, once happy hour rolls around, head to the northeast corner of the Rossio and Largo Sao Domingos. As the work day winds down, many of Lisbon’s resident immigrants from Portugal’s African colonies gather here for a shot or two of ginga, a sweet cherry liquor. Feel free to join in.
Following the drinks and people-watching, stop at the Rossio, make your way north along Avenida da Liberdade, downtown Lisbon’s leafy green main thoroughfare. Around the middle, turn left into Praca de Alegria and make your way to the Enoteca, a wine bar set in an 18th-century marble water pumping station. This is one of the best and certainly the most atmospheric place in Lisbon to sample the fine wines of Portugal, as well as to get a lite bite to eat.
After dinner, make your way back to Restauradores and the Elevador da Gloria, a funicular into Barrio Alto. From there, enjoy your fill of the cafes, bars, and clubs of Lisbon’s liveliest downtown neighborhood.
Travel down to the riverfront and the Cais do Sodre train station. From here, board not the train but the Number 15 Tram so as to enjoy more of the riverfront scenery on the way to Belem. Here, you will find the world’s finest example of Manueline architecture in the Jeronimos Monastery. Included in the complex are a maritime museum and an archaeological museum, so after the visit, you will probably need a snack. Walk two blocks east to Antiga Confeitaria de Belem, which has been serving their famous tarts filled with cream since 1837.
After the monastery and the tarts, walk downriver to the picture postcard-perfect Tower of Belem. The tower is bordered by a grassy park, as ideally suited to a rest as it is to gazing at the tower’s ornate, fairy tale-like architecture.
Once you are done with the tower, make your way to Belem Train Station and board a commuter train for Cascais and spend the afternoon at the beach. Just a few minutes from the station is the start of a promenade, which is lined with cafes and enjoys access to a succession of urban beaches all the way to Estoril. Keep walking until you find a patch of sand that suits you, and enjoy your Sunday afternoon at the beach.
When dinnertime rolls around, walk down to Estoril and almost the very end of the promenade to Opiparo, a lovely restaurant with a thoroughly Euromodern decor. Here you can enjoy a pleasant and very reasonably priced meal of fresh grilled fish or stewed rabbit while listening to the breaking waves.
Once dinner is complete, you can walk back along the promenade to Tamariz Beach, where there is an entrance for Estoril’s train station and take the train back to the city center and your hotel.