This post specifically lays out major attractions and a recommended itinerary based on the locations, operating hours, and amount of time spent at each. The days can be interchanged, just keep in mind a lot of monuments are closed Mondays, so save Day 3 or 4 for Monday (those are all open). Also recommend not staying out late the night before the Sintra day trip, unless you're crazy like me and say YOLO! For the full details on my trip to Lisbon, see this post .
Belem Tower / park (1 hr)
Jeronimos Monastery (2 hr)
Pasteis de Belem (30 min)
Lunch at Time Out Market (1 hr)
Pink Street for photos (30 min)
Sunset along Tagus River
Take a tuk tuk tour through Alfama and Chiado neighborhoods to see: Santa Luzia viewpoint, Senhora do Monte viewpoint, Lisbon Cathedral, Praca do Comercio (2-3 hrs)
Go to Santa Justa Lift and have bacalhau at the top of the lift (1 hr)
Visit Convento do Carmo right behind Santa Justa Lift (1 hr)
Day trip to Sintra - Get to Sintra at 9AM. I booked a private tour with Sophiatours. Here is their site or Trip Advisor. Pick up and drop off in Lisbon also available if you'd rather not take the train (~45 min ride for 5 euros roundtrip). Places to see:
Pena Palace - colorful, most popular palace in Sintra
Quinta da Regaleira - also popular for it's underground tunnels and initiation well
Monserrate Palace - beautiful Indian-influenced palace
Castelo dos Mouros - ruins of a Moorish Castle built in 9th century
Sintra National Palace - located in town
Cabo da Roca - cliff at the most western point of continental Europe
Castelo de San Jorge (1-2 hr)
COVID test (up to 1 hr depending on the line)
Sunset at Santuario de Cristo Rei / April 25th Bridge (3-4 hrs including round-trip travel)
Some night-time activities for any night:
See a fado show / dinner in Alfama - dinner, in general, runs late in Lisbon. I found fado shows scheduled until midnight!
Bars on Pink Street - but these ones are more expensive due to the location
Bars elsewhere - 2-3 euro beers and shots? Don't mind if I do!