Lisbon is well-connected and compact, making it possible to explore the city center and venture out to Sintra and seaside towns in just four days. This itinerary works well for a weekend getaway or as part of a multi-country European trip. The Old Town has many slopes, trams, and viewpoints—take your time and enjoy the walk while sampling local food.
Start at Praça do Comércio → Arco da Rua Augusta → Alfama (Lisbon Cathedral, narrow alleys, and fado taverns) → São Jorge Castle for panoramic views of the red rooftops → Take tram 28 to Graça → Watch the sunset from Miradouro de São Pedro in the evening, then find a small restaurant for live fado music. The day involves lots of walking, so watch out for steep slopes and cobblestone streets.
Jerónimos Monastery (UNESCO World Heritage Site, booking recommended) → Belém Tower → Padrão dos Descobrimentos (Monument to the Discoverers) → Belém Cultural Center → Try authentic pastel de nata at a historic bakery → In the evening, head to Cais do Sodré to see the Tagus River and the 25 de Abril Bridge. The Belém area is compact—you can visit the sites by tram or on foot along the river.
Take a train to Sintra: Start with Pena Palace (go early to avoid crowds) → Moorish Castle or Sintra National Palace → Visit Quinta da Regaleira to see the Initiation Well → In the afternoon, take a bus to Cape Roca (the westernmost point of mainland Europe, with views of the Atlantic and the famous “Here, where the land ends and the sea begins” monument) → Stop by the seaside town of Cascais on your way back to Lisbon.
Options include Évora (Bone Chapel and Roman Temple), Óbidos (a well-preserved walled town), or Cascais and Boca do Inferno. Return to Lisbon in the afternoon to pick up your luggage and head to the airport. If your flight is late, have dinner near Praça do Comércio before departure.