Perhaps it was what Lisbon had in common with San Francisco that first had me hooked.

A majestic suspension bridge painted a familiar shade of international orange? Check. Antique cable cars that rattle and shudder their way up steep city streets? Check. A treacherous position on a fault line, a long and storied seismic history, and one devastating earthquake that nearly burned the city to the ground? Check, check, and check.

In many ways, Lisbon is San Francisco’s worldly European cousin, but in so many others, the city is entirely its own. As one of the oldest cities on the continent, Lisbon has seen its turn as the leader of the Age of Discovery, the European center of a vast colonial trade network, and the capital of Portugal on the wide Rio Tejo. Its opulent wealth may be a thing of the past, but Lisbon’s well-worn charm and global flavor are as present as ever.

So pop a bottle of vinho verde and toast to the weekend ahead—we’re in Lisboa for the next three days.

FRIDAY

To My Big Brother Jorge, The Richest Man In Town

Since the time it was first settled in the 8th century B.C., the hill that overlooks central Lisbon has served as a strategic fortification for the Phoenicians, the Romans, and the Visigoths. But it was the invading Moors who built the stone castle on the hill in the mid-11th century—and the conquering forces of Dom Afonso Henriques, the first king of Portugal, who claimed it during the Reconquista in 1147.

The Castelo de São Jorge went on to house Portuguese kings for nearly four centuries, and it has since become an ideal introduction to the city below. Admire panoramic views, wander the surrounding lanes, and stop for breakfast at Café Audrey at the foot of the hill. With a postcard-perfect setting at the Hotel Santiago de Alfama, this charming café is the place for a coffee, a housemade pastry, or an afternoon drink in the shade—and you’ll likely be back for all three (Rua de Santiago 10 a 14).

The Hills Are Alive With The Sound Of Fado

With origins that date back to the Visigoth occupation, the Alfama is the oldest district in Lisbon—a confounding tangle of lanes that meander down the hillside to the Rio Tejo. Survey the scene from two of the city’s most beloved viewpoints—the Miradouro de Largo das Portas do Sol and the Miradouro de Santa Luzia—before diving into this traditional sailors’ quarter head first. Your eventual destination? The patio tables of Medrosa d’Alfama, where you can sip vinho verde, snack on grilled chorizo, and listen to fadistas in the courtyard singing songs of heartbreak and loss (Largo São Rafael 6).

SATURDAY

Ol’ 55

On November 1, 1755, as the Portuguese faithful attended mass on All Saints Day, a series of catastrophic earthquakes shook Lisbon. Churches crumbled the ground, more than 12,000 homes were destroyed, and the Rio Tejo transformed into a 20-foot tsunami that swallowed the city’s harbor.

The earthquake left an enduring mark on Lisbon, killing as many as 60,000 people and igniting fires that raged for days. It also led to the rebuilding of Baixa, the downtown commercial district distinguished by its 18th century buildings and sensible gridded roads. Spend a morning strolling between the riverfront Praça do Comércio and the bustling, oblong Rossio—and then get ready to head uphill.

Living La Vida Portuguesa

With its Parisian-style buildings and upscale boutiques, the chic hillside shopping district of Chiado has a way of taking you around the world. You’ll find tasty German sausages and charming ambience at Kaffeehaus, which sits in a tranquil plaza at the end of Rua Anchieta. A few doors down, A Vida Portuguesa is a one-stop shop for all things classically Portuguese, from fine soaps and lotions to toothpaste in vintage packaging (Rua Anchieta 11). And for more than 100 years, Café a Brasileira has served its signature bica (an espresso-like coffee) to poets and artists in grand art deco surroundings (Rua Garrett 120).

The Michelin Man

It’s up, up, up you go to the aptly named Bairro Alto, the vibrant “high town” perched above Baixa and Chiado to the west. Catch golden hour at the Miradouro de São Pedro de Alcântara and sit down for dinner at Bairro do Avillez, the newest outpost for revolutionary Portuguese cuisine by Michelin-starred chef Jose Avillez. Snag a seat in the casual front room taberna, grab a pencil for your menu, and choose your own culinary adventure—just don’t neglect the charcuterie, the pork steak, and the indulgent smoky tuna (Rua Nova da Trindade 18).

SUNDAY

Perhaps Vasco Was This Man’s Name

It was Prince Henry the Navigator who first envisioned Portugal’s role in what would become a legendary Age of Discovery. And by the end of the 15th century, Vasco da Gama had rounded the Cape of Good Hope to become the first European to reach India by sea. The success of da Gama, Ferdinand Magellan, and other Portuguese explorers ushered in a golden era of global commerce, vast riches, and celebratory architecture commissioned by King Manuel I.

There is no greater example of the ornate Manueline style than the Mosteiro dos Jerónimos, the grand limestone church and monastery in the Belém district west of central Lisbon. This UNESCO World Heritage Site features an awe-inspiring cloister and da Gama’s final resting place; it’s also a short stroll from the Torre de Belém, an intricate riverfront tower that once welcomed the great explorers home.

Insider Tip: The tower is most beautiful when the light is low at sunrise and sunset.

Mañana I’m Doing Nata

It is for the sake of your own waistline that you should wait until Sunday to visit Pastéis de Belém, the birthplace of Lisbon’s signature pastry in 1837. The rich egg custard and flakey tart shell of the pastel de nata might seem simple at first, but a sprinkling of cinnamon and sugar transform this humble pastry into an irresistible bite of French-toast-flavored goodness. And with the kitchen turning out nearly 20,000 pastéis per day, you’ll always get one fresh from the oven (Rua de Belém 84 a 92).

A Ribeira Runs Through It

With 24 restaurants, nearly a dozen shops and vendors, eight bars, and a music venue, the riverfront Mercado da Ribeira offers no shortage of variety. Whether you’re in the mood for steak, sushi, or a quick and casual bite, this century-old food market has been an epicenter of Lisbon cuisine since its 2014 redevelopment by Time Out Portugal (Avenida 24 de Julho). But if you’re feeling paralyzed by culinary indecision, fear not. The market is also a few blocks from Cantinho do Avillez, a modern and sophisticated member of the Avillez empire that will help you bid Lisbon a celebratory farewell (Rua dos Duques Bragança 7).

A Few Notes

Just as Lisbon is a town for walking, it’s also a town for Airbnbs. Consider the hilltop neighborhoods of Graça, where you’ll have easy, scenic access to the Alfama, and Príncipe Real, which is known for its upscale charm just north of the Bairro Alto. Add a private terrace to the equation and you’re set for the weekend ahead.

Photographs

TITLE: The beautiful Mosteiro dos Jerónimos | FRIDAY: A classic wall of painted tiles, or azulejos; walking the streets around the Castelo de São Jorge; castle hill; castle hill; a fountain on the Miradouro de Santa Luzia; flowers on the Miradouro de Santa Luzia; beautiful doors above the Alfama; the patio of Medrosa d’Alfama; Largo de São Miguel in the Alfama; the view of the Alfama from Miradouro de Largo das Portas do Sol | SATURDAY: Praça do Comércio; a trolley in Baixa; the Elevador da Santa Justa in Baixa; the streets of Chiado; a lovely doorway in Chiado; the Ascensor da Glória in the Bairro Alto | SUNDAY: The cloister at Mosteiro dos Jerónimos; Mosteiro dos Jerónimos; the church at Mosteiro dos Jerónimos; Torre de Belém; the view of Lisbon from Graça.