5 Days in Lisbon and Beyond
Most five-day Lisbon plans spend four days wandering the same three neighbourhoods and call the fifth a “day trip” almost as an afterthought. Flip that. Lisbon is a genuinely excellent base, not just a city, and this version spends one focused day on the city itself, then four days fanning out to Sintra, Cascais, Setubal and Obidos, four completely different versions of Portugal within striking distance of your hotel. For the city done properly instead, see our 7-day Lisbon itinerary ; for a shorter version of this same day-trip approach, our 3-day itinerary forces a single choice for day three.
Book these before you go:
- A Baixa or Chiado hotel : close to both train stations you’ll use most
- Pena Palace timed entry : book weeks ahead for Easter-October dates
- Setubal dolphin-watching tour : best booked before you land, it’s the one genuine sell-out risk on day four
- A guided Sintra day tour : the alternative to managing tickets yourself
| Day | Focus |
|---|---|
| 1 | The city, done properly, in one day |
| 2 | Sintra |
| 3 | Cascais |
| 4 | Setubal and Arrabida |
| 5 | Obidos |
Day 1: The City, Done Properly, in One Day
Start early in Baixa and Chiado, the flat downtown grid rebuilt after the 1755 earthquake. Rossio Square, Praca do Comercio by the river, coffee at A Brasileira if you want it. By afternoon, head into Alfama. Climb above the main tram route and the crowds fall away fast. Sao Jorge Castle at the top, around 15 EUR, the best rooftop view in the city, worth catching before sunset. Skip Tram 28 once it fills up, it’s the single worst pickpocket spot in Lisbon.
Should Belem make the cut on a trip this focused on day trips? No, and that’s deliberate. Belem’s two monuments both run timed entry and sit a tram ride out of the centre, easily three or four hours once you count travel and queueing, hours you don’t have when four of your five days are earmarked for the wider region. Our Lisbon guide covers it properly if you extend the city portion of a future trip.
Finish with a proper Fado dinner if you want the music, around 45 EUR for the full meal-and-show version or 17-20 EUR for tapas and wine.
Day 2: Sintra
Pena Palace requires timed, pre-booked entry through the official Sintra parks site . Walk-up access from Easter through October means hours in a queue or no entry at all. Train from Rossio, about 40 minutes, 2.45 EUR one way. Bus 434 covers the station-to-gate stretch, 4.10 EUR one way, 7.10 EUR round trip, or an unlimited day pass at 13.50 EUR, roughly double the stale ~6.90 EUR figure some older guides still quote. Combined palace-and-park entry is 20 EUR, park-only 14 EUR. If you’ve got energy left, Quinta da Regaleira nearby is a genuinely strange, worthwhile second stop, symbolic wells and all.
Day 3: Cascais
A completely different train line, from Cais do Sodre rather than Rossio, about 40 minutes out, roughly 2.25-2.45 EUR each way on a Zapping-loaded Navegante card. Walk the coastal promenade to Boca do Inferno, a collapsed sea cave where the Atlantic funnels through a narrow chasm, aim to arrive within two hours of high tide for real spray rather than quiet rocks.
Day 4: Setubal and Arrabida
Best reached by car or an organized tour rather than public transport, about an hour south along the Arrabida coast road. A dolphin-watching trip on the Sado estuary runs around 40 EUR for 2.5 hours, tracking a resident bottlenose population of roughly thirty animals, one of only three such resident colonies left in Europe, with sighting rates above 95%. Pair it with the Arrabida cliffs and some of the cleanest water near Lisbon, and eat choco frito, fried cuttlefish, in Setubal town itself, the local specialty.
Day 5: Obidos, Then Home
Skip the direct train, it’s a slow regional service that takes over two hours, runs only a few times a day, and drops you a 20-minute walk from the actual town. The Rodotejo express bus from Campo Grande station is the right call, about an hour, roughly 9.45 EUR each way, no return fare sold so buy two singles. Obidos itself is a walled medieval hill town, small enough to see properly in a morning, quiet enough that it barely feels like the same country as Alfama at noon.
Eat Right All Week
The pastel de nata rivalry is real: Manteigaria in Chiado versus the original Pasteis de Belem, both 1.30-1.50 EUR. Wherever you sit down for a proper meal, remember the bread and olives on the table are not free, that’s the couvert, usually 1-4 EUR, decline it before it’s touched if you don’t want it on the bill.
One Practical Note
Get a Navegante card, 0.50 EUR, and load Zapping onto it at your first metro stop. It covers the metro, trams, and both the Sintra and Cascais trains at a better rate than singles, and it’s the one piece of setup that makes every one of these five days run smoother.