Alfama
Alfama is the oldest neighborhood in Lisbon, surviving the 1755 earthquake more or less intact. Here's how we'd spend three days with a single base at Altura Alfama, starting with the sunrise light on the tile-fronted buildings and ending at a Fado house that locals actually go to.
Day one, the walk through Alfama
Start before breakfast with the stepped alleys around Largo de Santo Estêvão. Head to São Jorge Castle for the first morning light on the city below. Lunch at Prado on Rua das Pedras Negras, local sourcing, everything pan-sized. In the afternoon, take the 28 tram all the way up to Graça, which is where residents actually shop, and walk back down to the hotel in time for sunset on the terrace.
Day two, the estuary
Walk the riverfront from the Praça do Comércio out to the old warehouses of Cais do Sodré and the Time Out Market. We recommend the ferry across to Cacilhas for lunch at Ponto Final, tables at the water's edge with an unobstructed view back across to Lisbon. Afternoon in Belém, skipping the tourist pastel de nata line and instead going to Manteigaria.
Day three, Sintra or the Algarve
If you have energy for a full-day, Sintra is the unmissable move. Train from Rossio at 8 a.m. beats the coach-tour crowds to Quinta da Regaleira, after which you can walk up to Pena Palace. Alternatively, three hours south to the Algarve for a proper beach day, we'll arrange the driver.