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5 Days in Lisbon: Itinerary with Sintra and Cascais

By the Travel Portugal Now team · Published 2 October 2026

Five days in Lisbon gives you time to see the city properly, at a relaxed pace, and add the best day trips: Sintra, Cascais and the coast, or Arrábida’s beaches. Here’s our 5-day Lisbon itinerary.

Quick answer: Day 1: Alfama and the castle. Day 2: Belém. Day 3: Sintra. Day 4: Baixa, Chiado, Príncipe Real and a sunset sail. Day 5: Cascais and the coast, or Parque das Nações and the Oceanário. Evenings: fado, rooftop bars and Bairro Alto.

Lisbon

Day 1: Alfama and the castle

São Jorge Castle (€17), the Santa Luzia and Portas do Sol viewpoints, the cathedral and Alfama’s lanes. Fado at night. See Alfama and fado in Lisbon.

Day 2: Belém

Jerónimos (€18), Belém Tower (€15, timed), the Monument to the Discoveries, pastéis de Belém and the MAAT roof. Not on a Monday! See Belém.

Day 3: Sintra

Train from Rossio, then Pena Palace (book a timed ticket), Quinta da Regaleira and the old town. See Sintra in one day and Lisbon to Sintra.

Day 4: Baixa, Chiado and Príncipe Real

Praça do Comércio and the arch, Chiado’s cafés and the Carmo ruins, Príncipe Real’s gardens and shops, then a sunset sail on the Tagus or a rooftop bar. See Chiado and Bairro Alto, Príncipe Real and rooftop bars.

Day 5: Choose your own

Tips

Shorter trip? See 2 days or 3 days in Lisbon.

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