Portugal
🌊 5-Day Lisbon Itinerary
Seven hills, pastéis de nata, and fado
Your 5-Day Lisbon Plan
Five days allows you to add a Sintra day trip — one of Portugal's unmissable experiences — plus time to explore Chiado, Bairro Alto, and the waterfront neighbourhoods that reveal Lisbon's contemporary side.
Day 1
Alfama and São Jorge Castle
São Jorge Castle for morning views, then wander down through Alfama's lanes — the neighbourhood is best explored without a fixed route. Stop at the Museu do Fado for context before an evening Fado dinner.
Day 2
Belém Monuments
Early to Jerónimos Monastery, then Torre de Belém, the Monument to the Discoveries, and the MAAT contemporary art museum along the waterfront. Pastéis de Belém mandatory.
Day 3
Sintra Day Trip
The 40-minute train from Rossio takes you to Sintra, a UNESCO cultural landscape of fantasy palaces built into forested hillsides. Pena Palace (a fairytale extravaganza of colour and towers) and the Quinta da Regaleira (mysterious initiation well, esoteric gardens) are the highlights — book both in advance.
Day 4
Chiado and Bairro Alto
Chiado is Lisbon's most elegant neighbourhood — the Brasileira café (where Fernando Pessoa's statue sits at his favourite table), independent bookshops, and the best fashion boutiques. As night falls, Bairro Alto's bar scene begins — hundreds of small bars opening onto the streets, locals drinking on the pavement.
Day 5
Cascais Coast and Farewell
The 40-minute train to Cascais runs along the Atlantic coast — jump off at Estoril for the casino and gardens or continue to Cascais for the pretty harbour and Boca do Inferno cliffs. Return to Lisbon for a final sunset from the Miradouro da Graça viewpoint.
Other Itinerary Lengths
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