4 days in Lisbon

Morning

Castelo de São Jorge at opening

Be at the gate when it opens at 9:00 and you will have the ramparts and the best panorama in the city almost to yourselves before tour groups arrive around 10:30. Walk the battlements clockwise and finish at the shaded terrace with its resident peacocks.

Afternoon

Alfama lanes, Sé Cathedral and Santa Luzia

Drift downhill through Alfama's stairways via Miradouro de Santa Luzia and Portas do Sol, where the azulejo panels frame the river. Duck into the 12th-century Sé Cathedral on the way to Baixa; skip the packed Tram 28 here and simply walk, as everything is within 15 minutes on foot.

Evening

Fado dinner at Clube de Fado

Clube de Fado, tucked behind the cathedral, is one of the most respected fado houses in the city, with top-tier fadistas performing in a vaulted stone room. Book a table for 21:00 directly with the house, and keep silent during each set; locals take it seriously.

Morning

Jerónimos Monastery and Belém Tower

The Manueline cloister of Jerónimos is Lisbon's single most beautiful space; enter by 9:30 with a pre-booked ticket to avoid a queue that easily runs 45 minutes by mid-morning. Afterwards walk the riverfront past the Padrão dos Descobrimentos to photograph Belém Tower from the lawn rather than queueing to climb it.

Afternoon

MAAT rooftop and LX Factory

Walk the undulating roof of the MAAT for free river views, then hop on tram 15 to LX Factory, a converted 19th-century textile complex beneath the 25 de Abril Bridge. Browse Ler Devagar, the bookshop with a flying bicycle suspended from its ceiling, and grab a coffee in the old print hall.

Evening

Time Out Market and Pink Street

Head to Mercado da Ribeira in Cais do Sodré around 19:00, when the stalls are lively but you can still find seats, and graze across the city's best chefs under one roof. Finish with a ginjinha or a glass of vinho verde along Rua Nova do Carvalho, the pink-painted former sailors' street.

Morning

Pena Palace on the first time slot

Take the 8:00-ish train from Rossio and the 434 bus up the mountain to make the 9:30 Pena Palace entry, the slot that beats the day-trip coaches. Book the palace-and-park ticket in advance, as timed entries regularly sell out days ahead in high season.

Afternoon

Quinta da Regaleira's Initiation Well

Walk 20 minutes downhill through the Sintra village to Quinta da Regaleira and descend the spiralling Initiation Well, then follow the underground tunnels out to the lake. Mid-afternoon is quieter here once the morning tour groups have moved on.

Evening

Sunset at São Pedro de Alcântara

Back in Lisbon, ride the Glória funicular or walk up to Miradouro de São Pedro de Alcântara for golden-hour views across to the castle you climbed on day one. Then dine in Bairro Alto or nearby Príncipe Real before the area's late-night bar crowd arrives after 23:00.

Morning

Calouste Gulbenkian Museum and gardens

One of Europe's great private collections spans Egyptian antiquities to Lalique jewellery, and it is rarely crowded on weekday mornings. Leave time for the modernist gardens, which are free and among the most peaceful spots in the city.

Afternoon

Chiado and Baixa food walk

A small-group food walk is the fastest way to taste the city: think bifana sandwiches, Portuguese cheeses, tinned fish, ginjinha and a tawny port. Choose an afternoon departure through Chiado and Baixa and skip lunch beforehand, as tastings add up to a full meal.

Evening

Sunset sailing on the Tagus

A two-hour sailing trip from Doca de Santo Amaro glides past Belém Tower and under the 25 de Abril Bridge just as the city turns gold. Most departures include a glass of wine; bring a layer, as the river breeze is cool even in summer.