Lisbon 5-Day Itinerary

Start in Alfama, Lisbon's oldest neighbourhood, built on a hillside below the castle. Spend the morning getting deliberately lost in its stairways and lanes, then climb to São Jorge Castle for the ramparts and the widest view over the city and the Tagus.

In the afternoon, walk down to Miradouro das Portas do Sol and Miradouro de Santa Luzia, connected by a short tiled walkway, for two of the city's best viewpoints. Have dinner in Alfama and find a fado house for a late set — this neighbourhood, along with Mouraria next door, is where the music was born.

Take Tram 15E or the train from Cais do Sodré to Belém. Jerónimos Monastery is the centrepiece — a UNESCO World Heritage Site with Manueline cloisters that took a century to build. Book a timed slot online to skip the queue.

Walk the riverside to Belém Tower, then eat at Pastéis de Belém, open since 1837, for the original warm custard tart. Spend the afternoon at LX Factory, a converted industrial complex nearby with bookshops, design studios, and a rooftop bar under the 25 de Abril Bridge.

Morning: walk Baixa, the grid of streets rebuilt after the 1755 earthquake, down to Praça do Comércio on the river. Ride or admire the Elevador de Santa Justa, then move into Chiado for bookshops, theatres, and a coffee at Café A Brasileira.

Lunch at Time Out Market in Cais do Sodré. Afternoon in Príncipe Real, the city's most elegant neighbourhood, with its botanical garden and boutique streets. Evening: dinner off the main drag, then Bairro Alto for Lisbon's classic nightlife — small bars, cheap drinks, and narrow streets that fill up after 10pm.

Slow down. Miradouro da Graça and Miradouro da Senhora do Monte, a five-minute walk apart, are the city's best-value viewpoints and far less crowded than the Alfama miradouros. Spend the morning here with a coffee, then walk down into Mouraria, the multicultural neighbourhood next to Alfama where fado first took shape.

In the afternoon, ride Tram 28 for a stretch (early morning or after 6pm to avoid the crush) and visit the National Tile Museum, housed in a former convent, for 500 years of Portugal's azulejo tradition. Evening: a proper seafood dinner — grilled sardines if it's summer, bacalhau if it's not.

Sintra is a fairy-tale hill town 40 minutes from Lisbon by direct train from Rossio station, and it deserves the full day it demands. Go early — by 10am the crowds and the queues for palace shuttle buses are significant.

Pena Palace, a candy-coloured Romantic palace on the hilltop, is the headline sight — book timed tickets in advance. Quinta da Regaleira, with its symbolic initiation well and mossy grottoes, is stranger and just as memorable. If time allows, the Moorish Castle ruins above the town add a third, less crowded stop with sweeping views to the Atlantic.

Return to Lisbon by early evening train for a final dinner in the city — Chiado or Príncipe Real are good choices to close out the trip properly.