Lisbon Itinerary: A 5-Day Sample Plan and How to Build Your Trip

Quick answer: Five days in Lisbon: Alfama and São Jorge Castle with Tram 28, riverside Belém for the Jerónimos Monastery and custard tarts, downtown Baixa–Chiado–Bairro Alto, a Sintra palace day trip, and a final day at LX Factory and coastal Cascais.

Day 1 — Alfama & the Castle

Begin in Alfama, the tangle of medieval lanes that survived the 1755 earthquake. Climb early to São Jorge Castle (about €15) for ramparts and peacocks above a red-tiled sprawl, then wander down past the Sé de Lisboa cathedral and the tiled miradouros. Ride the famous Tram 28 at least one stop through Alfama’s hairpin turns — a single fare is about €3.30 on board, but load a rechargeable Viva Viagem card at any metro machine to pay less and skip queues. Board at Martim Moniz first thing, because by mid-morning the little wooden trams are jammed and pickpockets work the crush. For lunch, seek out grilled bacalhau (salt cod) at a tucked-away tasca. Insider tip: end at a fado house in Alfama after dark — ask about the smaller, dinner-optional rooms rather than the big tourist shows.

Day 2 — Belém by the River

Give the whole day to riverside Belém, the launching point of Portugal’s Age of Discovery. Take tram 15E from Praça da Figueira or the quick Cascais-line train from Cais do Sodé to Belém station. Start at the Jerónimos Monastery (about €18; free Sunday mornings, but expect a line), a Manueline masterpiece where Vasco da Gama is entombed. Then cross to the riverbank for the fortified Belém Tower (about €15) — it reopened in 2026 with timed-entry slots, so book a slot ahead to guarantee entry — and the sail-shaped Padrão dos Descobrimentos monument. The unmissable stop is Pastéis de Belém, the 1837 bakery serving the original warm custard tart dusted with cinnamon, about €1.50 each. Insider tip: skip the takeaway queue, sit in the tiled back rooms, and order your tarts with a bica (espresso) at the counter.

Day 3 — Baixa, Chiado & Bairro Alto

Spend today in the flat, grand heart of the city. Walk the Baixa grid rebuilt after the earthquake, from riverfront Praça do Comércio under its triumphal arch up pedestrian Rua Augusta. Ride the wrought-iron Santa Justa Lift (about €5.50 return, or free on a day travelcard) for a rooftop view, then drift into elegant Chiado for its bookshops and the A Brasileira café with its bronze statue of poet Fernando Pessoa. As evening falls, climb into bohemian Bairro Alto, where the shuttered streets come alive with tiny bars. Insider tip: order a chilled shot of ginjinha (sour-cherry liqueur) from a hole-in-the-wall stand near Rossio, then bar-hop with a plastic cup in hand as the locals do. For a memorable free finale, walk to the Miradouro de São Pedro de Alcântara for the sunset over the castle.

Day 4 — Sintra Day Trip

Escape to Sintra, a UNESCO hill town of fairy-tale palaces about 40 minutes inland. Catch the train from Rossio station (about €2.40 each way with your Viva Viagem card) and go early, as the narrow roads and shuttle buses clog by midday. Book a timed ticket for the candy-coloured Pena Palace in advance (about €20 for palace and park) — entry is only valid for your chosen slot. Pair it with the neighbouring Quinta da Regaleira, whose Initiation Well spirals underground through mossy tunnels. In the town centre, the twin white chimneys of the National Palace of Sintra mark the old royal kitchens. Insider tip: buy a travesseiro, Sintra’s flaky almond-cream pastry, from the historic Piriquita bakery, and take the local 434 bus up to Pena rather than walking the steep hill in the heat.

Day 5 — LX Factory & Cascais

On your last day, slow down. Start at LX Factory, a converted riverside industrial complex under the 25 de Abril Bridge, full of independent shops, street art, and a bookstore set in a former printing works — go for brunch and browsing. From nearby Cais do Sodé you can take the Cascais-line train (about €2.40) west along the coast to Cascais, a breezy former fishing town turned seaside resort with a pretty marina, small beaches, and the dramatic Boca do Inferno sea cave a short walk along the cliffs. Alternatively, spend the afternoon in the Time Out Market back at Cais do Sodé, where top Lisbon chefs run stalls under one roof (plates roughly €10–16). Insider tip: for one last view, ride up to the Cristo Rei statue across the river, or simply catch sunset from a Cascais beach with a final pastel de nata in hand.