A Stylish Weekend in Lisbon: Rooftops, Wine Bars, and Hidden Gems

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Advisor - Emily Giglio
Curated By

Emily Giglio

  • Lisbon

  • Portugal

  • City Travel

  • Food & Wine

  • Arts & Culture

  • Local Culture

Advisor - A Stylish Weekend in Lisbon: Rooftops, Wine Bars, and Hidden Gems
Curator’s statement

Lisbon is a city that awakens all the senses—vibrant yet relaxed, rich in history but pulsing with modern creativity. What makes it so special to me is the way every detail feels intentional: the warm-toned, tiled buildings, the thoughtful color palettes, and the way food and art coexist in everyday life. From bold wines and epically flavorful dishes to design-forward boutiques and breathtaking viewpoints, Lisbon celebrates beauty, flavor, and soul in equal measure. I curated this guide to reflect that spirit—for travelers who seek inspiration in the small moments, and joy in the details.

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Day 1: Rooftop arrival, wine, and Petiscos

Morning

Settle into your chosen hotel and enjoy a leisurely start with a local espresso.

Lunch with a view

Dine at Java Rooftop, where contemporary cuisine meets stunning city panoramas. Savor dishes like grilled prawns and fresh salads while soaking in the views.

Afternoon

Explore the chic neighborhood of Príncipe Real. Visit Embaixada, a 19th-century palace-turned concept store featuring Portuguese designers and artisans. Don’t miss Malala Vintage, a curated trove of retro treasures, from denim jackets to statement accessories.

Pre-dinner bites

Sip Portuguese wines at ByTheWine Lisboa, and share octopus carpaccio, Iberian ham, and local cheeses in a romantic, cave-like space.

Dinner

Enjoy a relaxed yet refined meal at Tapisco, where Chef Henrique Sá Pessoa presents a fusion of Portuguese and Spanish tapas. Recommended dishes include:

  • Tomato Bread with Jamón Ibérico de Bellota

  • Octopus Salad with vinaigrette and smoked paprika

  • Huevos Rotos with Iberian Paletilla, onion and red pepper sofrito

Pair your meal with a classic Pisco Sour.

Day 2: Cultural exploration & culinary delights

Morning

Take a taxi to Belém. Indulge in a warm pastel de nata from Pastéis de Belém, then visit the Jerónimos Monastery and the MAAT Museum for a dose of history and contemporary art.

Lunch

Cross the river to Ponto Final in Almada for a waterfront lunch featuring grilled fish and crisp white wine, accompanied by views of Lisbon’s skyline.

Afternoon

Return to the city and wander through LX Factory, a vibrant hub of creativity with indie boutiques, street art, and unique cafes.

Dinner & movie night

Head to Magnolia for an intimate dinner showcasing seasonal Portuguese cuisine. Afterward, enjoy an open-air screening at Black Cat Cinema, Lisbon’s coolest outdoor cinema experience, often hosted on rooftops or hidden courtyards with wine and cozy blankets provided.

Day 3: Brunch & books, last-minute finds

Brunch

Start your day at Liberty: Brunch, Coffee & Books, a cozy spot near Avenida da Liberdade. The raspberry and pistachio latte, French omelette, and pancakes are to die for.

Late morning

Stroll Avenida da Liberdade for a final hit of Lisbon’s charm. Stop into A Vida Portuguesa for beautifully packaged soaps, ceramics, and culinary souvenirs.

Sweet treat

Before departing, visit Manteigaria to sample their acclaimed pastéis de nata. With multiple locations across Lisbon, including Chiado and Time Out Market, it’s convenient to grab one (or a few) of these custard tarts, known for their flaky crust and creamy filling.

Departure

Lisbon’s airport is a quick 15–20 minute ride—giving you time to sneak in one last miradouro moment before heading home.

Day 4: Across the river for long lunches & laidback views

Late morning

Sleep in, grab a coffee to go, and take your time soaking in the last hours of Lisbon. Then, head down to Cais do Sodré and hop on the ferry across the Tagus River to Cacilhas—just 10 minutes away, but it feels like a world apart.

Lunch with a view

Dine at the iconic Ponto Final, dramatically perched at the edge of the river with unmatched views back toward the city. Order the arroz de polvo (octopus rice), grilled dourada, and a crisp white wine. Time slows down here—it’s the perfect spot for a long, leisurely lunch in the sun.

Afternoon stroll & relaxation

Walk along the waterfront past the old warehouses and fishermen’s piers until you reach the River Garden (Jardim do Rio). It’s a peaceful place to sit under the trees, journal, read, or just watch the ferries come and go. If you’re still craving something sweet, grab an ice cream or pastel de nata from a nearby kiosk.

Golden hour return

Take the ferry back in time for golden hour. If you have energy left, cap off the day with one last rooftop toast—maybe back at Java, or try Topo Chiado near the Carmo Convent for a different angle on the city.

Need to know

  • Reservations: Book ahead for popular spots like Java, Tapisco, Magnolia, and Black Cat Cinema.

  • Vintage finds: Malala Vintage is best in the afternoon when the shop is fully open and curated.

  • Weather watch: Bring a light jacket for Black Cat Cinema. Lisbon nights cool down even in summer.

  • Shoes matter: Lisbon’s hills and cobblestones require comfortable soles.

  • Culinary delights: Don’t miss out on Lisbon’s signature pastries and wines—they’re integral to the city’s culture.

  • Skip Alfama: You’ve got views, food, and design elsewhere—no need to follow the tourist trail.

Advisor - Emily Giglio

Travel Advisor

Emily Giglio

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For more inspiration and insider recommendations, visit our Lisbon page.