Exactly where to walk, run, and eat like a local
Lisbon gives you the good kind of sensory overload, from its brightly colored tiles, medieval marvels, green wines, and fresh seafood. Still, it's small and walkable, even considering the near-vertical hills; they’re a bonus for your glutes. In 48 hours, you can see it all—and spend a few at the beach.
Where to Stay
On a longer visit it would make sense to stay in a central neighborhood like Bairro Alto, Chiado, or Baixa, but for a two-day trip, it’s also worth considering the left-of-center Alcântara or Belém. You’ll be heading that direction for one of the two days, plus it’s a quiet escape from the late night revelry in the center. It’s also on a better stretch of waterfront running trails if you’ll prioritize that each morning. Try Altis Belém Hotel for scenic views and luxe amenities.
If you opt for the heart of the city, the Memmo Príncipe Real will give you equally lovely views, plus a rooftop pool. Or, check into The Independente Hotel to feel like you’re on set of a vintage Wes Anderson flick, ready to escape into the bustle of cable cars and cobblestone streets.
Day 1
Start the day with a Portuguese breakfast at The Mill; the fresh-baked queijada cheese breads promise extra stair-climbing fuel but healthy options, like a peanut butter porridge with omega seeds, abound. Then, you’ll follow Calçada do Combro east while exploring whichever meandering side streets call your name. Keep going east to the commercial center, with very non-commercial highlights like Praça Luís de Camões, a square commemorating the famous Portuguese poet, and Convento do Carmo, the barely standing remains of an enormous convent that crumbled in Lisbon’s earthquake of 1755. There's plenty of shopping but don't miss Pop Closet for trendy new and thrifted clothes.
Make your way south at Rua Augusta, through the arc that bears the same name, and into Praça do Comércio, which hosts the city’s biggest festivals and outdoor concerts. From there, go east along the waterfront to Rua Arameiros and into Alfama. The destination is St. George’s Castle atop the hill, but you’ll want to take your time exploring Alfama’s crooked, hilly side streets. Detour for lunch at the tiny Lisboa Tu e Eu, where you can befriend neighboring tables as the chef prepares sardines and gazpacho.
The castle itself, with a foundation built around 48 BC, was passed between Romans, Visigoths, Moors, and Christians. Now, it’s one of Lisbon’s most beloved relics. After exploring it, walk back along the water for some vinho verde at Time Out Market.
Dinner is at Adega Machado in the historic city center. Go around 9 p.m. for a famous Fado accompaniment from soul-bearing folk singers. Fado is all about saudade, the longing for days past.
Day 2
Get yourself to Belém in the morning—via taxi, train, or foot—and start with a smoothie bowl at SUD Lisboa. Then walk a few minutes along the water so that you can marvel at the Tower of Belém, a 16th century seaside watchtower. Take a quick tour of Jerónimos Monastery, a massive architectural wonder built between 1501 and 1601. If time allows, visit the infamous Pastéis de Belém just a block away, for their namesake two-bite cream cakes.
Hop the westward train to Cascais, a humble beachside town just 30 minutes away. Stop for lunch at Polvo Vadio (get the squid), then spend a few hours on the beach, where you can get in some stretching and yoga or just relax under an umbrella with a good book.
Catch the train back into the city, all the way to the last stop, Cais do Sodré. Make your way to the bohemian Taberna Rua das Flores for a fresh seafood dinner. Afterwards, get lost in the side streets of Bairro Alto, following the crowds to the dozens of bars that litter the side streets. It doesn’t matter where you go: Order a drink to go, take it to the streets, and mingle with the Portuguese until your 48 hours are up.