Some people love hop-on-hop-off tour buses, enabling them to see all the hot spots of a city in a day or two. We get it, sometimes you just don’t have any time. But there are better ways to holiday-cram than a big red bus. Like this walk between two of greater Lisbon’s most popular destinations — Sintra and Cabo da Roca.
The walk only takes about four hours, so depending on when you start your day, you should be able to see much of Sintra’s old center and possibly a site or two such as Quinta da Regaleira before setting off. The hike itself passes by many of Sintra’s other famed landmarks such as the Moorish castle and Pena Palace, so with a little side-stepping, you can see it all!

Start at the train station (assuming you are arriving from Rossio in Lisbon) and make a sharp left to immediately hit very steep hills. Get used to it. On the plus side, as you climb, you are greeted with beautiful views of Castelo dos Mouros and the valley. You’re heading to the castle, and at this point, it is all paved roads and relatively easy going. As you walk, you pass by interesting but rarely visited spots such as Igreja de Santa Maria and Quinta de Santa Maria. Feel free to take a moment to check them out.
Eventually, you get to the castle grounds. Now, the way marked on the GPX track passes through an area that is currently “closed.” Use this at your own risk, you can always go around. But, if you do walk the lesser-trod path, you are rewarded with a chance to peer into one of Sintra’s little dark doors that seem to burrow into every hillside (you’ll know what that means soon enough).
If you want, take some time to explore the castle grounds, and even the castle itself (tickets required), before passing through toward Palácio Nacional da Pena. You’ll notice that as you exit the castle grounds, the walk takes you to the right while the palace itself is to your left. But, in the words of They Might Be Giants, “You’re not the boss of me now!” If you want to go to the palace, you do just that.

Continuing the walk, your meandering road passes through fields of boulders with private drives shooting off either side and patches of forest. If you turn around here, you get a very good view of Pena palace. After a long hike, you get to a crossroads, and most paths lead to where you want to go. But dead ahead is a forest road, which simply seems more interesting.
You stay in the forest on footpaths, bike tracks, and forestry roads until you reach Azoia. It is a short drop back into civilization, passing along the outskirts and the bizarrely-themed Moinho Dom Quixote, until the road turns back into a dirt path and eventually into a goat track.

The track takes you along cliff tops and valleys as you approach Cabo da Roca and is probably one of the wilder sections of the walk. With loose rock, high cliffs, and more succulents than you can count, make sure not to lose your footing or be too distracted by the magnificent coastal views.
Eventually, you emerge victorious on the large rocks that top the final cliff of Europe. Take a moment to enjoy the scene, since as you start to climb, the tourists — who number in their hundreds — will surely block the view.
From Cabo da Roca, you can take the 403 bus back to Sintra or, for a relatively quicker journey, to Cascais, where the train takes you to Cais do Sodre. It is worth noting that even if you got a Lisbon to Sintra return train ticket, it can be changed in Cascais for no extra cost (or at least it could in February 2019, you know bureaucracy).
Want to get freaked out before walking alone through the woods of Sintra? Check out the myths, legends, and paranormal activity that swirl around the area.
If you fancy taking the walk, the GPX track can be found here.