Most people visiting Lisbon spend at least one day in Sintra.
If you enjoy walking, there is a beautiful way to explore it without taking the bus directly from the station to the main monuments.
Take the train from Rossio Station in Lisbon to Sintra. From the station, walk towards the historic centre, around 15 minutes away.
On the way, I would stop at Casa Piriquita for a travesseiro, one of Sintra's traditional pastries. You'll need some energy for what comes next.
From the historic centre, walk to Largo Ferreira de Castro. This is where the Vila Sassetti route begins.
The trail is completely free and climbs for around 1.8 km through one of the greenest parts of Sintra. The official route takes around 45 minutes.
Vila Sassetti was built at the end of the 19th century as a summer residence for Victor Carlos Sassetti. It was designed by Luigi Manini, the Italian architect and scenographer who later worked on Quinta da Regaleira.
The house was inspired by the castles of Lombardy, and the gardens were designed around the natural landscape. As you climb, you pass small ponds and little waterfalls, winding paths, huge rocks and dense vegetation.
Further up, the trail passes Penedo da Amizade, a large granite rock that has long been a well-known place for climbers, before continuing through the forest towards the top of the hill.
The walk is mostly uphill, so I recommend proper shoes. It is manageable if you are comfortable walking, but the official difficulty is moderate. One of the things I particularly like is how fresh it feels under the trees, even on a warm summer day.
When you reach the top, you have a choice.
You can visit the Moorish Castle, a fortress founded around the 10th century during Muslim rule. Its walls follow the granite ridge and offer some of the best views over Sintra. The adult ticket currently costs €12.
Or you can continue towards the Park and Palace of Pena. The same Vila Sassetti route gives access towards both monuments. If you want to enter the palace itself, I strongly recommend booking in advance because palace entry uses a specific time slot.
If you have enough time, you can of course visit both.
For the way back you can descend on the other side using the Santa Maria Trail. It is a marked 1.77 km walking route connecting the Moorish Castle and Pena area with São Pedro de Sintra. From there, you can walk back towards the historic centre. This makes the day feel much more like a loop and lets you see a different part of the Sintra hills.
Once back in the centre, I would stop for lunch and enjoy Sintra without rushing.
And if you still have time and energy, Quinta da Regaleira is a great way to finish the day. It is within walking distance of the historic centre, so it fits naturally at the end of this route. I would book your ticket in advance and check your entry time before planning the rest of the day.
You really don't have to do everything.
You can visit the Moorish Castle, choose Pena instead, visit both, add Regaleira later, or simply enjoy the hike and spend more time in town.
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