Sintra is around forty minutes from central Lisbon by train, so the travel is trivial and the day is about how many palaces you can sensibly fit into it. This plan takes five, plus the westernmost point of mainland Europe, which is ambitious but workable if you start at nine and keep moving. The hills, not the distances, slow people down.
Is it worth a day trip?
Yes, and it is one of the best days out from any European capital: a romantic palace painted yellow and red on a ridge, a Moorish fortification along the ridgeline above it, a subterranean initiation well, and a botanical garden around a Mughal-influenced villa.
Be honest about the pace. Six stops is a lot and each involves a climb or a bus. With small children, or if you would rather see two things properly than six quickly, cut it to Pena, Regaleira and the town.
Stay overnight instead if you want Pena at opening without the day-trip crowd, or to walk the trails between the monuments rather than ride the bus. The trade-offs are in how far is too far for a day trip.
Getting there
Trains are run by CP, Comboios de Portugal, on the Sintra line. Services leave Lisbon from Rossio, Oriente and Entrecampos, take around forty minutes, and run every fifteen to thirty minutes. Use a rechargeable Navegante card from the station machines.
Sintra station is neither in the old town nor anywhere near Pena, and local transport is by Scotturb bus. The 434, the Pena circuit, runs one way only: station, Sintra Vila, the Moorish Castle, then Pena. Coming down from Pena it does not stop at the Moorish Castle again, it goes straight to Sintra Vila and the station. That is the most important thing to know about your day.
The 435 is the other circuit: station, Sintra Vila and the National Palace, Quinta da Regaleira, Seteais and Monserrate. Day tickets for each are sold on board or online from Scotturb. Cabo da Roca sits outside both circuits and is served by the 1624 route towards Cascais, run by Carris Metropolitana.
Pena down to the Moorish Castle is a short walk along the ridge, the old town to Quinta da Regaleira about ten minutes. Regaleira to Monserrate is kilometres of narrow road with no pavement, so take the bus.
The day, hour by hour
09:00 Pena Palace. Ferdinand II built this on the ruins of a monastery in the 1840s and painted it: ochre yellow, terracotta red, tiled domes, a triton over an archway, battlements never meant to defend anything. The bus drops you at the park gate, not the palace, and from there it is an uphill walk of fifteen to twenty minutes through the woods, with a small shuttle covering the last stretch for an extra fare. Your ticket is for a set time, so allow for the climb.
11:00 Moorish Castle. Walk down from Pena along the marked path to the tenth-century fortification that runs the ridge in two lines of wall. You climb the ramparts themselves, which rise and fall over the rock, taking in Pena above, the old town below and the Atlantic west. Uneven underfoot, so the wrong stop for sandals.
12:30 Sintra National Palace. Back down to Sintra Vila on the 434. This is the oldest surviving royal palace in Portugal, recognisable from anywhere in town by its two enormous white conical kitchen chimneys. Inside, the tiled rooms are the draw, particularly the Magpie Room and the Coats of Arms Room. Lunch in the town around it: a queijada or a travesseiro from an old pastry shop.
13:30 Quinta da Regaleira. Ten minutes' walk west, a romantic estate laid out around 1900 by a wealthy collector with a taste for symbolism. The Initiation Well is the famous part, an inverted tower sunk into the ground with a spiral staircase leading to tunnels that surface elsewhere in the garden. There is no lift, the steps are damp and queues form. Give it ninety minutes.
15:30 Monserrate Palace. The 435 carries on west to a nineteenth-century villa built for a British merchant family, its plasterwork and arches drawn from Mughal and Moorish architecture. The park is the real reason to come: one of the most important botanical collections in Portugal, laid out by species across a valley.
17:00 Cabo da Roca. The westernmost point of mainland Europe, a headland of cliffs high above the Atlantic with a lighthouse and a stone marker carrying a line from Camões. Getting there means the 1624 bus towards Cascais, so check the timetable and last return first. It is usually windy, and a fitting end to the day.
What to book ahead
Pena Palace needs a date and time slot, bought in advance from Parques de Sintra. Quinta da Regaleira is run separately, with its own official ticket office, worth using in high season. The Moorish Castle, the National Palace and Monserrate can normally be bought on the day, though combined tickets cost less than singles.
Open this day trip in Tralendr
All six stops are saved as a plan, pinned on a map, which helps here more than almost anywhere: the monuments look close together and are separated by steep hills and one-way bus routes.
Open the Sintra day trip plan. It opens in a browser without an account and you can change it: cut Cabo da Roca if the bus times do not work, or drop Monserrate and give Regaleira the afternoon. Send the link on and the others see the same map.
Worth reading first: how to plan a day trip for the last-train arithmetic, and all our day trips for the rest of the series.