Lisbon, Portugal 6 Day Itinerary

There is no train that runs directly between Sintra and Cascais, and this trips up more people planning a combined day trip than anything else on this list. Rossio Station only serves the Sintra line. Cascais and Estoril trains leave from Cais do Sodre, a completely different station on the other side of the city. If you want both towns in one day, you need to route back through central Lisbon, or accept that a 24-hour transport pass covering both lines, roughly 11 euros, is the more sensible way to do it than trying to string a direct connection together that does not exist.

Day 1: Arrival and Baixa

Land at Lisbon’s Humberto Delgado Airport, check into a centrally located hotel in Baixa or Chiado so you can walk to most of what follows, and use the afternoon to shake off jet lag with a loop through Rossio Square, Commerce Square, and the Rua Augusta Arch, which you can actually climb for a rooftop view over the plaza and river.

If you plan to ride Tram 28 at any point this trip, and you should, do it early morning or after 6pm rather than midday. It runs the most tourist-heavy loop in the city, through Alfama, Graca, and Baixa, and local police reported a real rise in tourist-area theft on this exact route in recent years, mostly slash-and-grab thefts during the crowded boarding and alighting at packed stops. Keep your phone in a front pocket, not a back one, and skip it entirely if a car pulls up already packed shoulder to shoulder, there will be another one along shortly.

Day 2: Belem and Alfama

Start in Belem, easily reached by tram or a short taxi ride. Belem Tower and the Jeronimos Monastery are both UNESCO listed and both worth entering rather than just photographing from outside, though lines build fast by mid-morning in high season, so aim to arrive close to opening. Pasteis de Belem, the original custard tart bakery dating to 1837, does get long queues, but the takeaway counter around the side moves much faster than the sit-down cafe if you just want the tarts and not the seating.

In the afternoon, head into Alfama, Lisbon’s oldest neighborhood and the one that survived the 1755 earthquake mostly intact, which explains why its streets still wind in a pattern no city planner would design today. Sao Jorge Castle sits above it all with the best panoramic view in the city, arrive later in the afternoon for softer light over the rooftops. In the evening, a proper Fado performance, ideally in a small, family-run venue rather than a dinner-show tourist trap, is one of the more genuinely moving things you can do in this city, the music is built entirely around longing and it lands harder live than any recording conveys.

Day 3: Modern Lisbon and LX Factory

Spend the morning at MAAT, the riverside museum of art, architecture, and technology, its curved roof alone is worth the walk along the water even before you get inside. LX Factory, a former industrial complex now packed with design shops, galleries, and cafes, makes an easy lunch stop, the space works because it never got over-polished into a shopping mall the way similar redevelopments elsewhere often do.

For dinner, head to Cais do Sodre, Cervejaria Ramiro is the standard recommendation for seafood in this city and it earns the hype, though be prepared for a wait even with a reservation, and note the seafood is priced by weight, which can surprise people expecting a fixed menu price.

Day 4: Sintra and Cascais

Take the train from Rossio to Sintra, it is the direct, no-nonsense route and departures run frequently through the morning. Pena Palace requires online, timed-entry tickets bought at least a day ahead, full palace and park access runs about 20 euros, park-only closer to 10 to 14 euros, and the on-site ticket office sells out during peak season, so do not plan on buying at the gate. Quinta da Regaleira, with its symbolic initiation well spiraling underground, and the Moorish Castle ramparts round out a full morning, you will not comfortably fit all three plus lunch and Cascais in one day without rushing, so pick two of the three Sintra sites and accept that.

For the afternoon, get back to central Lisbon and catch a separate train from Cais do Sodre out to Cascais, about 35 to 40 minutes and a couple of euros each way. Cascais rewards an unhurried beachfront walk more than a checklist of sights, it is a genuinely different pace from Sintra’s crowded palace paths. Return to Lisbon for dinner in Chiado, a neighborhood that does old-world cafe culture, Nicola among the historic ones, better than almost anywhere else in the city.

Day 5: Oceanarium and slower pace

The Lisbon Oceanarium, one of the largest in Europe, is worth a slower, unhurried morning rather than a rushed hour, the central tank alone holds species from four different ocean ecosystems in one connected space. Have lunch back in Belem if you want another crack at the tarts, or head to Bairro Alto for something different. In the afternoon, Eduardo VII Park gives one of the best formal green-space views over the city toward the river, and Bairro Alto’s bars, quiet by day, fill up properly after dark if nightlife is part of your plan for the evening.

Day 6: Last morning and departure

Use the morning for whatever got missed, a last coffee in a favorite square, a final round of shopping in Chiado, or simply retracing a walk you liked earlier in the week before heading to the airport.

A genuinely useful buy for this whole trip is the Lisboa Card, starting around 31 euros for 24 hours with longer options available, it bundles free public transport including the airport metro connection and the trains to both Sintra and Cascais, plus free entry to over 50 museums and monuments. Run the math against what you actually plan to see, for a itinerary this packed with paid sights it usually pays for itself well before day three. Lisbon is genuinely hilly in the older neighborhoods, pack shoes that can handle cobblestones and inclines, and keep transit or a taxi in reserve for the days your legs give out before your itinerary does.