5 Days in Lisbon: Itinerary with Sintra and Cascais

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.

Why five days works

Lisbon is hilly, so sightseeing takes longer than the map suggests. Five days lets you spend three days in the city and two outside it, without rushing. It also gives you a spare morning if it rains or if a palace is fully booked.

Day 1: Alfama and the castle

Start early at São Jorge Castle, before the crowds, and walk the walls for views over the river. Allow about 1.5 hours. Then walk down through the Santa Luzia and Portas do Sol viewpoints to the cathedral, and get lost in Alfama’s lanes. Tram 28 runs through the area, but it is packed in the middle of the day, so ride it early or late. In the evening, book a fado dinner in Alfama. See Alfama, the São Jorge Castle guide and fado in Lisbon.

Day 2: Belém

Take tram 15 or the Cascais-line train to Belém. Visit Jerónimos Monastery at opening, then the Monument to the Discoveries and the Belém Tower, which reopened in May 2026 with timed entry and a daily visitor cap, so book ahead. Have custard tarts at Pastéis de Belém and finish on the MAAT roof by the river. Most Belém monuments close on Mondays, so don’t plan this day for a Monday. See Belém and the Jerónimos guide.

Day 3: Sintra

Take the train from Rossio station to Sintra, about 40 minutes. Go straight to Pena Palace for your timed slot, then walk down to the Moorish Castle or take a bus or tuk-tuk to Quinta da Regaleira. Finish in the old town with a travesseiro, a puff pastry filled with almond cream. Two palaces is plenty for one day. See Sintra in one day and Lisbon to Sintra.

Day 4: Baixa, Chiado and Príncipe Real

Start at Praça do Comércio and walk through the arch up Rua Augusta. Climb on foot to Chiado for coffee and the Carmo ruins, a church left roofless by the 1755 earthquake. Carry on uphill through Bairro Alto to Príncipe Real’s gardens and shops. The Glória, Bica and Lavra funiculars and the Santa Justa lift have been closed since the September 2025 accident, so walk or use the metro (Baixa-Chiado station has long escalators up the hill). End with 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

• Cascais and the coast: beaches, Boca do Inferno and Guincho. The train from Cais do Sodré takes about 40 minutes and follows the coast. See Cascais.
• Parque das Nações: the Oceanário and the riverside cable car. Easy by metro to Oriente. See Parque das Nações.
• Arrábida: turquoise beaches and dolphins. Easiest by car or on a tour. See Setúbal and Arrábida.
• Museums and markets: the Gulbenkian, the tile museum, then LX Factory’s shops and cafes. See Lisbon on a rainy day.

What to eat

• Grilled sardines in early summer, especially around the June festivals.
• Bacalhau (salt cod) in its many forms.
• A bifana (pork sandwich) for a cheap lunch.
• Ginjinha, the cherry liqueur, sold by the glass near Rossio.

When to go

Spring (April to June) and early autumn (September to October) are the most comfortable months. June brings the Santo António festival, with street parties in Alfama. July and August are hot and busy, and winter is mild but rainier. See the best time to visit Lisbon.

Tips

• Lisboa Card: useful for your busiest sightseeing days. See is it worth it?
• Getting around: see Lisbon public transport and Lisbon trams.
• Book ahead: Sintra palaces, the Belém Tower and fado dinners all sell out in summer.
• Shoes: wear comfortable shoes with grip. The stone pavements get slippery.
• Where to stay: see where to stay in Lisbon.
• Food: a food tour on day one helps you order for the rest of the trip. See food tours.

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

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