Lisbon is Europe’s sunlit storyteller—rebuilt after the 1755 earthquake, powered by the Age of Discoveries, and wrapped in blue‑white azulejos that turn walls into archives. Its seven hills hide miradouros (viewpoints) where you can sip espresso and watch the Tagus River slip to sea. Around each corner you’ll hear saudade in a fado melody, smell grilled sardines, and spot a vintage tram rattling by.

Across four days, you’ll taste both the capital’s modern pulse and timeless neighborhoods—Alfama, Baixa, Chiado, and Belém—plus a day in Sintra’s misty palaces and Cascais’ seaside elegance. Expect cobblestones, stairways, and postcard sunsets; pack comfortable shoes and a light jacket for breezy evenings.

Practical notes: English is widely spoken, cards are accepted nearly everywhere, and the metro is clean and straightforward. Keep an eye on your belongings on crowded trams, especially Tram 28. For sweet fuel, compare the city’s two pastel de nata legends—Pastéis de Belém and Manteigaria—and decide your winner.

Lisbon

Why go now: Lisbon balances deep history with creative energy—tile museums next to street art, 16th‑century monasteries beside a cutting‑edge riverside museum (MAAT). Atlantic light makes every hour photo‑worthy.

• Top sights: Alfama’s lanes and viewpoints (Portas do Sol, Santa Luzia), Castelo de São Jorge, Sé Cathedral, Baixa and Praça do Comércio, Chiado, Elevador de Santa Justa, Belém Tower, Jerónimos Monastery, MAAT, LX Factory.
• Signature experiences: ride iconic Tram 28 early morning, hear live fado after dinner, and taste pastéis hot from the oven.
• Dining mood board: seafood at bustling cervejarias, modern Portuguese petiscos, Michelin‑minded tasting menus, rooftop sundowners with river views.
• Fun fact: Lisbon is one of Europe’s oldest capitals—older than Rome—and its glinting river “Tejo” once launched Vasco da Gama’s fleet.

Where to stay (handpicked):

• Four Seasons Hotel Ritz Lisbon (resort‑style city icon with a rooftop track and art deco flair): Check availability
• Olissippo Lapa Palace Hotel (a serene palace with gardens and a pool in refined Lapa): Check availability
• Martinhal Lisbon Chiado Family Suites (best for families—kitchenettes, kids’ club, central Chiado): Check availability
• Lisbon Destination Hostel (stylish hostel inside Rossio Station—great for social travelers): Check availability
• Browse more Lisbon stays on Hotels.com or apartments on VRBO.

Getting there and around:

• Flights (to/from Europe): Compare fares on Omio Flights. Typical times: Paris–Lisbon ~2h30, London–Lisbon ~2h45, Rome–Lisbon ~3h. Off‑season deals often from ~$60–$120 each way.
• Flights (long‑haul): For routes from North America, South America, Africa, or Asia, search Trip.com Flights or Kiwi.com. NYC–Lisbon nonstop ~6h45–7h30; West Coast via connections ~13–15h.
• Airport to city: Metro (Aeroporto–Baixa/Chiado) ~30 min, ~€2; rideshare ~20–30 min, ~€10–20 depending on traffic.
• Trains and buses in Europe: If you’re pairing Lisbon with other European cities, compare Omio Trains and Omio Buses for schedules and deals.

Day 1: Arrival, Alfama First Impressions, and Fado Night

Morning: Travel to Lisbon and check in. If your room isn’t ready, leave your bags and set out lightly. Grab a specialty coffee and pastel de nata at Manteigaria (watch the bakers torch natas behind glass) or try single‑origin pours at Fábrica Coffee Roasters on Rua das Portas de Santo Antão.

Afternoon: Wander Alfama, the city’s oldest quarter. Start at Miradouro das Portas do Sol for terracotta rooftops and the Tagus, then slip down to Sé Cathedral and the medieval lanes. For a relaxed orientation that conquers the hills, book this private tuk tuk experience:

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

In four hours you’ll hit Alfama, Baixa, Chiado, and Belém highlights with stories that anchor you for the days ahead—ideal on arrival day.

Evening: Make it a fado evening in Alfama. For dinner with music, reserve at Clube de Fado (classic, intimate) or Mesa de Frades (a tiny chapel with candlelit sets). Prefer a low‑key meal first? Try Zé da Mouraria for garlicky clams and oven‑baked cod, or Taberna da Rua das Flores (ever‑changing chalkboard of creative petiscos; arrive early to queue). Nightcap at Topo Martim Moniz with a skyline view.

Day 2: Belém Monuments, Riverfront Design, and a Lisbon Food Tour

Morning: Start with brunch‑style plates at Hello, Kristof (Scandi‑Portuguese vibes) or Seagull Method Café (shakshuka, pancakes, strong coffee). Tram 15E or a short rideshare takes you to Belém. Visit the Jerónimos Monastery (Manueline splendor, Vasco da Gama’s tomb) and stroll to the Belém Tower. Don’t skip warm pastries at Pastéis de Belém, baking since 1837—sprinkle cinnamon and powdered sugar for the classic finish.

Afternoon: Walk the riverside to the sculptural MAAT (Museum of Art, Architecture and Technology) for rooftop photos, then continue to LX Factory under the red 25 de Abril Bridge. Browse Ler Devagar (cathedral‑like bookshop inside a former press), sample croquettes at Crocante, and sip a craft beer at 1300 Taberna’s bar or a coffee at Wish Slow Coffee House.

Evening: Dive into Lisbon’s culinary scene with this award‑winning small‑group tour (four seated tastings, wines, and neighborhood storytelling):

Winner 2025 Undiscovered Lisbon Food & Wine Tour by Eating Europe

If you’d rather dine independently, book Cervejaria Ramiro for garlic shrimp, percebes, and buttery scarlet prawns (finish with a prego steak sandwich), or Solar dos Presuntos for seafood rice and Minho classics. Drinks after? Rooftops like Park (on a parking garage) or Topo Chiado overlook the lit‑up castle.

Day 3: Sintra & Cascais Small-Group Day Trip

Spend the day among palaces, cliffs, and coastal promenades on a comfortable small‑group tour with a guide (usually 8–20 people). Door‑to‑door logistics, skip‑the‑line strategies, and local stories keep the pace smooth. Expect ~9 hours.

Sintra and Cascais Small-Group Day Trip from Lisbon

Highlights typically include Pena Palace (hilltop Romantic fantasy), Sintra’s historic center (try Casa Piriquita for travesseiros and queijadas), and Cabo da Roca, continental Europe’s westernmost point. End in Cascais with time for gelato at Santini or seafood at Mar do Inferno by the surf, before returning to Lisbon early evening.

Independent option: take the train to Sintra from Rossio (~40 min, ~€2.50 each way) and to Cascais from Cais do Sodré (~40 min, ~€2.25 each way)—compare regional timings on Omio Trains. Go early to beat queues at Pena; book palace entry slots in advance when possible.

Day 4: Chiado, Convent Ruins, Last Bites, and Departure

Morning: Ride vintage Tram 28 from Martim Moniz to Campo de Ourique just after sunrise to avoid crowds, then breakfast at Dear Breakfast (eggs any way) or Heim Café (thick toast, smoothie bowls). Back in Chiado, browse Bertrand (the world’s oldest operating bookstore) and artisan shops on Rua Garrett.

Afternoon: Visit the open‑air Convento do Carmo—roofless Gothic arches frozen since 1755, with a small archaeological museum. For a view without the elevator queue, take the free terrace entrance behind the convent that looks across to the Santa Justa lift. Lunch at Time Out Market (aim for chef stalls like Marlene Vieira for seafood, Henrique Sá Pessoa for modern Portuguese, and Conserveira de Lisboa for tinned‑fish bites). Pick up last gifts: canned fish, olive oil, fleur de sel, or Ginjinha cherry liqueur for home.

Evening: Departure day—if time allows, espresso at A Brasileira or a final nata at Manteigaria. Metro to the airport is ~30 minutes; rideshare ~20–30 minutes depending on traffic.

Optional add‑ons if you have extra time: Tile‑painting workshop, National Azulejo Museum, Oceanário (world‑class aquarium), or a sunset cruise on the Tagus.

Booking logistics recap:

• Hotels: Four Seasons Hotel Ritz Lisbon, Olissippo Lapa Palace, Martinhal Chiado, Lisbon Destination Hostel, or browse on Hotels.com and VRBO.
• Flights: Europe routes via Omio Flights; long‑haul via Trip.com or Kiwi.com.
• Trains/Buses in Europe and to Sintra/Cascais: compare with Omio Trains and Omio Buses.
• Tours: Tuk tuk city intro, food tour, and Sintra & Cascais day trip via the Viator links above.

Where to eat and drink (save this list):

• Breakfast/coffee: Fábrica Coffee Roasters; Hello, Kristof; Seagull Method Café; Heim Café; Manteigaria (nata + espresso).
• Lunch: Time Out Market chef stalls; Tascardoso in Príncipe Real (hearty daily specials); A Merendinha do Arco (old‑school tasca near Rossio).
• Dinner: Cervejaria Ramiro (seafood temple); Taberna da Rua das Flores (creative petiscos); Zé da Mouraria (traditional Portuguese); A Cevicheria (Peruvian‑Portuguese mash‑up beneath the octopus installation); Bairro do Avillez (multiple concepts under one roof).
• Fado: Clube de Fado; Mesa de Frades; A Baiuca (tiny, convivial).
• Sweet stops: Pastéis de Belém (Belém); Manteigaria (multiple locations); Santini (gelato, Cascais and Chiado).

Three curated Viator experiences featured in this plan:

• True 4Hour Private Tuk Tuk Tour: Discover Lisbon with a Local!
• Winner 2025 Undiscovered Lisbon Food & Wine Tour by Eating Europe
• Sintra and Cascais Small-Group Day Trip from Lisbon

With four days, you’ll taste Lisbon’s neighborhoods, tuck into unforgettable seafood and sweets, and step into Sintra’s storybook hills before toasting the Atlantic at Cascais. It’s a compact Portugal itinerary that balances big‑ticket sights with local texture—one you’ll want to repeat with friends in tow.