Portugal rewards curiosity. Romans and Moors left their mark; the Age of Discovery launched caravels from the Tagus; today, you’ll find tiled facades, soulful fado, and markets brimming with Atlantic seafood. In one compact country, you can taste centuries of history—and a glass or two of velvety port.

This weeklong itinerary focuses on two icons—Lisbon and Porto—with a day devoted to Sintra’s palaces and the seaside town of Cascais. Expect hilltop viewpoints, neighborhood cafés, azulejo-lined churches, and a day in the Douro Valley, the world’s first demarcated wine region.

Practical notes: book top sights (Jerónimos Monastery, Pena Palace, Livraria Lello) in advance, watch for pickpockets on crowded trams, and pack comfy shoes for cobblestones. For intercity travel, Portugal’s trains are fast and scenic; food-wise, try grilled sardines, caldo verde, and pastel de nata wherever you go.

Lisbon

Lisbon is a city of seven hills, miradouros (viewpoints) at every turn, and tramlines threading through neighborhoods that feel like villages. Alfama survived the 1755 quake and still sways with fado; Belém recalls the explorers who sailed toward the unknown.

• Top sights: Castelo de São Jorge, Alfama lanes, Praça do Comércio, Belém’s Jerónimos Monastery and Tower, MAAT, LX Factory.
• Food & drink: Pastéis de Belém custard tarts; seafood at traditional cervejarias; natural-wine bars in Príncipe Real; petiscos (Portuguese tapas) in Chiado.
• Fun fact: Tram 28 dates back to the 1930s—ride early to avoid queues and enjoy the best city cross-section.

Where to stay (Lisbon): Luxe heritage at Four Seasons Hotel Ritz Lisbon; riverside grandeur at Olissippo Lapa Palace Hotel; family-friendly suites at Martinhal Lisbon Chiado Family Suites; budget-social at Lisbon Destination Hostel. Browse more stays: VRBO Lisbon or Hotels.com Lisbon.

How to get here: Fly into Lisbon (LIS). If you’re coming from within Europe, search fares on Omio Flights (Europe). From outside Europe, compare on Trip.com Flights or Kiwi.com.

Day 1: Arrival in Lisbon, Baixa to Alfama

Afternoon: Arrive and check in. Shake off the flight with an espresso and a pastel de nata at Manteigaria (watch the bakers torch the custard). Stroll Baixa’s grid to the riverfront Praça do Comércio, then ride the elevator or hike to the Miradouro de Santa Luzia for terracotta rooftops and the Tagus view.

Evening: Dinner options: Taberna da Rua das Flores (daily chalkboard of seasonal petiscos; arrive early), Cervejaria Ramiro (legendary garlic clams and scarlet prawns), or Zé da Mouraria (home-style cod). End with a fado set in Alfama—intimate rooms like Clube de Fado pair music with grilled fish and Douro reds.

Day 2: Lisbon Icons + Tuk Tuk Orientation

Morning: Get your bearings on a lively tuk-tuk circuit—historic hills without the uphill slog.

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

Afternoon: Tram or rideshare to Belém. Visit Jerónimos Monastery’s cloister, the Discoveries Monument, and Belém Tower. Refuel at Pastéis de Belém (order a warm box to go) and, if time allows, dip into MAAT’s contemporary galleries and rooftop curve for river panoramas.

Evening: Explore Príncipe Real’s wine bars. Try tapas-with-a-twist at Tapisco or seafood at Sea Me (razor clams and cuttlefish “spaghetti”). Nightcap at Pavilhão Chinês, a quirky bar-museum lined with vintage curios.

Day 3: Alfama to Chiado on Foot + Food & Wine

Morning: Beat the crowds on Tram 28 from Graça toward Estrela—ride a few stops, then walk back through Alfama’s lanes to Castelo de São Jorge for citywide views. Coffee at Fábrica Coffee Roasters; browse azulejos at the National Tile Museum if ceramics call your name.

Afternoon: Taste Lisbon with a local expert: classic tascas, hidden taverns, and neighborhood stories folded into every bite.

Lisbon Small-Group Portuguese Food and Wine Tour

Evening: Head to LX Factory for indie shops, street art, and a sunset drink at a rooftop. Dinner at A Cevicheria (Portuguese-Peruvian plates, octopus tartare) or neighborhood favorite Bairro do Avillez for wood-fired piri-piri chicken and seafood rice.

Day 4: Sintra Palaces & Atlantic Cliffs (Day Tour)

Spend the day among Romantic-era palaces and coastal cliffs. This small-group tour bundles timed entries and the best viewpoints, saving you from the Sintra logistics maze.

Lisbon: Sintra, Regaleira, Pena, Cabo Roca All Tickets Included

Expect forested paths at Quinta da Regaleira (seek the Initiation Well), candy-colored Pena Palace high above the mist, the wind-whipped cliffs of Cabo da Roca, and a relaxed stroll in Cascais. Back in Lisbon, celebrate with grilled seabass at Cais do Sodré’s Marisqueira Azul or piri-piri chicken at Bonjardim; for dessert, try gelato at Nannarella.

Porto

Porto rises steeply above the Douro: tiled churches, ironwork balconies, and the Dom Luís I Bridge linking the city to Vila Nova de Gaia’s port lodges. The city’s character is hearty—think francesinha sandwiches, riverside taverns, and sunset cruises under six bridges.

• Top sights: Ribeira waterfront, São Bento Station’s azulejo hall, Clérigos Tower, Livraria Lello, Bolsa Palace, port wine cellars in Gaia.
• Food & drink: Pork-sandwich perfection at Casa Guedes (with Serra cheese); petiscos at Taberna dos Mercadores; craft coffee at Combi; creamy eclairs at Leitaria da Quinta do Paço.
• Fun fact: The Douro became the world’s first demarcated wine region in 1756—centuries before modern appellation laws.

Where to stay (Porto): Wine-country views above Gaia at The Yeatman; contemporary comfort at HF Ipanema Park; design-forward budget dorms at Gallery Hostel; great-value central at Moov Hotel Porto Centro. Browse more stays: VRBO Porto or Hotels.com Porto.

Getting there from Lisbon: Take the Alfa Pendular or Intercidades train (about 2h45–3h10) to Porto-Campanhã, then a short hop to São Bento. Check schedules and fares (~€15–€40 depending on advance purchase) on Omio Trains (Europe). Buses also run in ~3.5 hours via Omio Buses.

Day 5: Lisbon to Porto, Ribeira & Gaia Cellars

Morning: Depart Lisbon after breakfast; aim for a mid-morning train so you’re in Porto by early afternoon. Grab pastries for the ride—try a queijada or a ham-and-cheese tosta.

Afternoon: Check in and walk the Ribeira riverfront, noting the colorful facades and rabelo boats. Cross the lower deck of Dom Luís I Bridge to Gaia for a port lodge tour and tasting—Graham’s offers vineyard panoramas; Sandeman dives into tawny vs. ruby styles.

Evening: Dinner at Brasão Cervejaria Aliados (sharing plates and a francesinha with proper beer pairing), or seafood rice at Adega São Nicolau. For a cozy wine bar in a former chapel, slip into Capela Incomum.

Day 6: Douro Valley Wine Day (Vineyards, Lunch & River)

Trade city streets for terraced vines on an all-day Douro immersion—two estates, a regional lunch, and a gentle boat ride from Pinhão. Pickup and transport are included, so you can focus on scenery and tastings.

Authentic Small Group Douro Wine Tour with Lunch & River Cruise

Expect to learn about schist soils, the role of the Douro in port and dry wines, and the centuries-old practice of foot treading in lagares. Back in Porto, keep dinner light—Taberna dos Mercadores (tiny; arrive early) or a cheese-and-charcuterie board with a glass of Douro red.

Day 7: Porto Markets, Tiles & Farewell

Morning: Coffee at Combi Coffee Roasters or 7g Roasters, then wander the revamped Mercado do Bolhão to sample cured meats, pão de ló, and fresh fruit. Swing by São Bento Station’s blue-and-white tile panels, and if lines are short, pop into Livraria Lello (time-slot booking recommended).

Afternoon: Early lunch before departure: Casa Guedes for the pork-and-Serra-cheese sandwich, or Cantinho do Avillez for refined Portuguese plates. Head to the airport or station for your onward journey—use Omio Flights (Europe), Omio Trains, or long-haul options via Trip.com Flights or Kiwi.com.

Evening: If you have extra time, toast the trip with a quick sunset drink along the Douro—then it’s time to say até logo.

Optional/Alternate Experiences You Can Swap In

• Porto city immersion including Lello, a river cruise, and cable car: Porto Walking Tour, Lello Bookshop, River Cruise and Cable Car

  

• Douro alternatives from Porto: Complete Douro Valley Wine Tour with Lunch, Wine Tastings and River Cruise

  

Logistics Tips

• Transit cards: In Lisbon, load a Viva Viagem card for metro, tram, and bus; in Porto, the Andante card covers metro and buses. Both cities are very walkable—pack grippy shoes for hills and slick cobbles.
• Dining: Many traditional spots don’t take reservations; arrive early (by 7 pm) or plan for a short wait. Lunch menus are often the best value.
• Bookings: Prebook Sintra’s Pena Palace, Jerónimos Monastery, and Livraria Lello where possible, and lock in Douro tours a week or more ahead in peak season.

Summary: In one week, you’ll ride Lisbon’s hills, taste your way through its neighborhoods, wander Sintra’s storybook palaces, and settle into Porto’s riverside rhythm—capped by a day among the Douro’s terraces. Expect unforgettable views, soulful music, and memorable plates from morning espresso to late-night petiscos.