Lisbon, the seven-hilled capital draped in azulejos, has been welcoming sailors, poets, and sweet-toothed travelers since the 15th-century Age of Discoveries. You’ll feel its maritime past in Belém’s grand monuments and along the breezy Tagus Riverfront, and its soul in Alfama’s fado-lined lanes.

Between tiled palaces and modern design museums, Lisbon is a food lover’s playground: grilled sardines in summer, creamy pastéis de nata any time, and petiscos (Portuguese tapas) made for sharing with friends. Coffee culture is strong, brunch is excellent, and local wines—Vinho Verde to Dão reds—are affordable and flavorful.

Practically speaking, Lisbon is compact, safe, and easy to navigate by metro, tram, and inexpensive ride-hailing. Wear good shoes for cobblestones, keep an eye on pockets on packed trams, and grab a 24-hour transport pass if you plan to hop between neighborhoods. This plan balances relaxed mornings, scenic viewpoints, and memorable meals—perfect for four best friends reuniting.

Lisbon

Lisbon blends old-world neighborhoods—Alfama, Mouraria, and Graça—with artsy districts like Príncipe Real and Santos, plus the creative complex of LX Factory. Miradouros (viewpoints) offer postcard panoramas: Senhora do Monte at golden hour is magic.

Top must-sees include Jerónimos Monastery and Belém Tower, the National Tile Museum for azulejo lovers, MAAT for striking contemporary architecture, and the lively Time Out Market, where top chefs run casual stalls. Tram 28 clatters through the city’s historic heart—ride early to avoid crowds.

• Best neighborhoods to stay (Airbnb/VRBO-friendly): Príncipe Real (upscale, leafy, great boutiques); Chiado (central, elegant, walkable); Baixa (flat streets, transport hub); Santos/Estrela (calmer, café-filled); Campo de Ourique (local, great food market); Lapa (residential, quiet). Avoid the noisiest parts of Bairro Alto if you’re light sleepers.
• Coffee & brunch gems: Fabrica Coffee Roasters (specialty beans), The Mill (Aussie-Portuguese brunch), Hello, Kristof (Scandi vibe), Fauna & Flora (beautiful plates), Copenhagen Coffee Lab (multiple locations), Wish Slow Coffee (LX Factory).
• Local flavor: Try a shot of ginjinha (cherry liqueur), split a seafood feast at Cervejaria Ramiro, and sample tinned fish conservas as gifts. For shopping, browse A Vida Portuguesa, Embaixada (concept stores), and the Tuesday/Saturday Feira da Ladra flea market.

Where to book your stay: For apartments and townhouses ideal for a group of four friends, browse VRBO Lisbon. Prefer hotels? Compare options on Hotels.com Lisbon.

• Splurge: Four Seasons Hotel Ritz Lisbon (resort-style rooftop track, spa, art collection).
• Classic elegance: Olissippo Lapa Palace Hotel (garden pool, quiet Lapa).
• Great for groups/families: Martinhal Lisbon Chiado Family Suites (apartment-style units, central).
• Budget & social: Lisbon Destination Hostel (in Rossio station, stylish common areas).

Getting to Lisbon: If you’re flying within Europe, compare fares and times on Omio flights. From outside Europe, check Trip.com or Kiwi.com. Typical flight times: 2–3 hours from Paris/London/Madrid; ~7–8 hours from NYC; ~11 hours from São Paulo.

Local transport: The Aeroporto–city metro takes ~25 minutes to Saldanha (~€2). Taxis/ride-hail into the center are usually €15–25. Consider a 24-hour transit pass (metro/tram/bus) if you’ll ride often.

Day 1: Arrival, Baixa & Chiado Stroll, Foodie Evening

Afternoon: Land and check in. Shake off travel with an espresso and pastel de nata at Manteigaria (watch the custard tarts come out piping hot). Wander Baixa’s grand squares—Praça do Comércio and Rossio—then glide up the Santa Justa Lift area for views (skip the lift line; use the free Carmo side walkway). Browse the world’s oldest bookshop, Bertrand (1732), in Chiado.

Evening: Toast your reunion on a relaxed, sit-down food crawl that dives into authentic neighborhoods:

Winner 2025 Undiscovered Lisbon Food & Wine Tour by Eating Europe

Expect four proper dine-in stops—think cheese and charcuterie, petiscos, and regional wines—plus local stories that set the tone for your trip. Not doing a tour? Book a progressive dinner: start with tinned fish at Sol e Pesca, share pica-pau beef at Taberna da Rua das Flores, and finish with ginjinha near Largo de São Domingos.

Day 2: Belém Icons, Riverside Design, LX Factory, Sunset Sail

Morning: Fuel up at The Mill (great flat whites and eggs with chorizo) or Dear Breakfast. Head to Belém early: tour Jerónimos Monastery’s Manueline cloisters and step onto the riverside at Belém Tower for history and breezes. Line up for Pastéis de Belém—the original custard tarts since 1837; sprinkle cinnamon and share a warm box among friends.

Afternoon: Walk the river path to MAAT for striking curves and rooftop views. For lunch, choose O Navegador (grilled fish) or Pão Pão Queijo Queijo (quick bifana/sandwiches). Continue to LX Factory in Alcântara: browse indie shops, hit Ler Devagar bookstore’s photogenic staircase, and settle at Wish Slow Coffee for a cold brew. If you’re craving museums, the National Coach Museum’s gilded carriages are nearby.

Evening: Unwind on the water as the city glows gold:

Lisbon Sunset Sailing Tour with White or Rosé Wine and Snacks

Glide past the 25 de Abril Bridge and Cristo Rei statue, sipping local wine with light bites. After docking, dinner near Cais do Sodré: try Sea Me (modern seafood and sushi), Pharmácia (playful petiscos in a former pharmacy), or Time Out Market for a choose-your-own feast—Pap’Açorda for prawns à la açorda and Marlene Vieira for seafood rice.

Day 3: Day Trip to Sintra, Cabo da Roca & Cascais (Light Hiking + Beach)

Trade city hills for fairy-tale palaces and Atlantic cliffs on a small-group excursion that keeps logistics easy and the pace relaxed:

Sintra and Cascais Small-Group Day Trip from Lisbon

Typically 8–9 hours, this tour covers Pena Palace (vivid colors, misty forests—bring layers), Sintra’s old town for travesseiros (almond pastries), Cabo da Roca (continental Europe’s westernmost point, with short cliff walks), and free time in Cascais to dip your toes at Praia da Rainha. Wear comfy shoes; trails around Pena Park make for easy, scenic strolls.

Back in Lisbon, celebrate with a seafood spread at Cervejaria Ramiro (garlic clams, scarlet prawns; arrive early or late) or a shared petiscos table at Bairro do Avillez. Nightcap at Park Bar (rooftop over a parking garage) or Topo Chiado with Carmo Convent views.

Day 4: Alfama, Miradouros, Tuk-Tuk Finale & Departure

Morning: Start with specialty coffee at Fabrica Coffee Roasters (try a Portuguese toast with queijo and honey). Hop the iconic Tram 28 from Martim Moniz to Graça before crowds; hop off to admire Miradouro da Senhora do Monte and Miradouro da Graça. If it’s Tuesday or Saturday, browse the Feira da Ladra flea market for vintage tiles and curios.

Late Morning: Cap your reunion with a breezy, no-sweat city spin perfect for four friends:

True 4Hour Private Tuk Tuk Tour: Discover Lisbon with a Local!

Zip between Alfama’s lanes, Sé Cathedral, Portas do Sol, Bairro Alto, and Príncipe Real without the uphill slog—guides weave in history and photo stops. Alternatively, if you’re craving one last museum, the National Tile Museum (in a former convent) is a serene stunner.

Lunch & Departure: Keep it close to your lodging: Zé da Mouraria (hearty Portuguese plates), Tasca da Esquina in Campo de Ourique (chef Vítor Sobral’s petiscos), or a light bite at Nicolau. If time allows and the sun’s out, a super-quick beach fix is possible: train from Cais do Sodré to Carcavelos (~30 minutes, ~€2–3) for a sandy stroll, then head to the airport.

Extra Ideas to Personalize

• Cooking & hands-on fun: Join a pastel de nata or Portuguese cooking workshop (available most days in central Lisbon). Great bonding activity for a friends’ trip.
• Fado evening (low-key): Book an early set in Alfama for soulful live music with grilled fish and vinho verde.
• Parks & easy hikes: Monsanto Forest Park offers shady trails and city views; along the coast, walk the flat seaside promenade from Cascais to Estoril.

Shopping Hit List

• A Vida Portuguesa: Beautifully curated soaps, tins, notebooks—ideal gifts.
• Embaixada (Príncipe Real): Concept stores inside a 19th-century palace.
• Conservas shops: Colorful tins of tuna, sardines, and mackerel to take home.
• LX Factory: Indie fashion, design objects, and weekend markets.

Practical Getting Around

• From airport: Metro Red Line to Saldanha/Baixa (~€2, 25–30 minutes) or taxi/ride-hail (€15–25, 20–30 minutes).
• Public transit passes: A 24-hour ticket often pays off if you’ll take metro + trams the same day.
• Day trip to Cascais (DIY): Train from Cais do Sodré to Cascais (~40 minutes, ~€2–3). For Europe-wide trains/buses, check Omio trains and Omio buses; ferries (like Cacilhas) via Omio ferries.

Budget Tips (Target: 50/100)

• Mix sit-down dinners with casual gems: bifanas (pork sandwiches), tasca lunches, and Time Out Market for variety.
• Choose 1–2 paid tours (food + sunset sail or Sintra) and otherwise enjoy free viewpoints and museums with discounted passes.
• Share petiscos and seafood platters; Portuguese portions are generous.

Dining Shortlist by Mood

• Seafood classics: Cervejaria Ramiro; Marisqueira Azor (Cais do Sodré); Baía do Peixe (Cascais for “rodízio de marisco”).
• Modern Portuguese: Bairro do Avillez (multiple concepts in one space); Zunzum Gastrobar (river views, creative small plates).
• Tascas & petiscos: Zé da Mouraria; Taberna da Rua das Flores; Tasca da Esquina (Campo de Ourique).
• Sweet stops: Pastéis de Belém; Manteigaria; NATA de Lisboa (easy grab-and-go).

How to book transport for this itinerary: For flights in Europe use Omio flights; long-haul options via Trip.com or Kiwi.com. Trains and buses around Portugal and Spain are on Omio trains and Omio buses.

This four-day Lisbon itinerary layers easy sightseeing with memorable meals, a story-rich food tour, and a breezy sunset sail—plus a day in Sintra and Cascais for palaces, cliffs, and beach time. You’ll head home refreshed, well-fed, and stocked with sweet pastries and even sweeter shared memories.