Located about an hour from Lisbon, Sintra is a town dominated by palaces. Over hundreds of years, different leaders have built their fortresses on top of these lush mountains. Some chose Sintra because it is near the sea, which allowed for vast trade route and its high cliffs provide a natural defense. Others, hoped these towering heights and mythic history would bring them closer to God. Regardless of which you believe, stepping into the city center, there is an undeniable magnetic force drawing you up to the mountains.
Though it feels like a completely different world, Sintra is only an hour from Lisbon, making it great for a day trip or a weekend. Having gone for a day trip, I would strongly recommend staying over in Sintra so you can see everywhere on your list.
To get to Sintra from Lisbon, you'll want to take the train. Russo Station is situated in a grand square with fountains. monuments, and an intricate title pattern. Train tickets are sold upstairs from automated ticket counters or a line of tellers behind glass. The day I went in June, both options had lines so long they went outside of the main ticket lobby. Luckily, I was traveling with 2 companions so we could each get in a line (two for the automated ticket counters and 1 for the in-person window). That day, the automated ticket counter lines were shorter, but took much longer than the in-person ticket counter. Plus, the woman behind the counter was able to get us the best deal for the tickets and explain where to catch the right train.
The train ride is about an hour through other cities and suburbs. It isn't incredibly scenic and may be a bit crowed depending on the time of day. However, it shows you a bit more of Portugal than you would have seen otherwise.
Lisbon is an orange city. The air is dry and golden, roofs are terra cotta, and buildings are painted bright warm colors. Sintra on the other hand, is most definitely green. From the moment you step off the platform, the air is humid and teaming with life.
From the platform, you'll need to decide how you want to travel. Keep in mind that no matter how you go, most of the mountain roads are one way, so you will need to plan your day accordingly. The cheapest way around is by bus, which you can pick up from the town center. On the end end of the spectrum are a number of bus or Segway tours, guide for each will be swarming the station offering the best deals.
For the first day, I would recommend you pack a lunch and take the local 434 tourist bus up the mountain to save some money at the start. However, you can't miss taking a tuk tuk down the windy mountain roads on the way back down!
Day 1
Castelo dos Mouros
The first stop on your trip is the to Castelo dos Mouros. Built by the Moores in 700-800s, this castle was part of a vast kingdom stretching up from Northern Africa. Its inhabitants changed over time as various groups were conquered until the castle fell into disrepair after a large earthquake. Eventually, King Ferdinand II rebuilt the castle, which has views to and from his beloved Pena Palace that you will visit next.
Palacio Nacional de Pena
The Place de Pena is probably the first thing that will pop-up when researching Sintra. This whimsical palace mixes ornate tiles with bright primary colored clay walls to create a castle unlike any you've seen before. From the outside, Pena Palace almost looks like 3 castles morphed into one, but walking around you'll start to piece the floor plan together.
The park offers two types of tickets depending on how much you want to see and how much you want to spend. One ticket is for the park and entrance into the palace. It is more expensive but is the only way to see the state rooms, kitchen, and cloister in the monastery. The cheaper option is entrance to park, which allows you to see the terraces around the palace and the old chapel, which makes you feel like you are inside the palace itself. I went with just the park pass, found the hidden path up to the terraces, and loved it! My suggestion: don't be afraid to take the road less traveled when walking in the park!
Speaking of the park, I would plan on spending some time moseying around the palace grounds. There's a lot to see from gardens to ponds to other historic buildings waiting to be discovered in the green labyrinth. If you packed your lunch, find a bench and enjoy the sunshine. If you didn't, there is a cafeteria in the palace with rooftop seating overlooking the castle and park, though finding a seat here can be a challenge.
Another great spot within the park is Cruz Alta, the highest point in Sintra. From here you can see Pena Palace in all of its glory, the Atlantic Ocean, and, if you're lucky on a clear day, Lisbon (or so I've heard)!
Palácio Nacional de Sintra
Spend the afternoon exploring one more royal palace! The National Palace of Sintra is a wildly different feel from the other 2 castles you've seen today. This palace has a stronger lived-in vibe, with grand halls and sitting rooms that take you back to medieval times. One of the biggest sights in this castle, is all of the tile work. The internet is full of photos of people in front of the blue and white titled church in Porto or buildings covered in tiles with the most beautiful patterns in Lisbon, and this museum gives you a taste of when that passion for tiles began.
Evening
When you've finished visiting the National Palace, spend the rest of the evening walking around the town center and soaking in the history. At this point, you've seen three different eras in Sintra and have a bit more context for its present day shops and restaurants, so take some time to explore the area. Be sure to eat a big dinner and get some rest. Today was a lot of walking around and tomorrow will be too!
Day 2
Get ready for another time traveling day! You'll want to bring your walking shoes, camera, and a beach towel. Today's trip will require a couple of local buses or a few hired tuk tuks, so have some cash ready.
Quinta da Regaleira
This mansion is one of the spookiest places I've ever been. Build relatively recently in 1910 by a rich businessman, it looks like a haunted manor from a forgotten time. Inside and around the grounds are hidden details calling to the Freemasons, Knights of Templar, and Rosicrucians. Hidden in the expansive greens are two "Initiation Wells" that bring you deep into the rock for a symbolic ceremony no one can explain. Stemming from each well are a series of elaborate tunnels. Parts are lit from the ground, throwing shadows on the rock cut walls that bring ghosts to life around every corner. Venturing out of the yellow light, you can walk for what feels like miles deep underground looking for signs of ancient alchemy.
Lunch
Grab lunch a little while up the road from the castle at Dona Maria. This upscale restaurant has a great view over the town center and the National Palace of Sintra. On a nice day, you can sit outside and soak in the views, and in less than ideal weather, you can sit inside and enjoy the renaissance art covering the walls.
Palace of Monserrate
Making your way out of the city, head to Palace of Monserrate. The lace-like intricacies of each archway and stunning stonework are an architecture's dream, while the sprawling gardens around the palace are heaven for botanists! Built as a vacation home for Sir Francis Cook, this palace was heavily influenced by Arabic designs and Portuguese romanticism, making it look like it stepped out of a tale from Arabian Nights.
Cabo da Roca
Spend the rest of the afternoon at the beach a bit outside of Sintra. Watch the waves crash on sand in a little paradise next to a few hundred feet of dramatic cliffs. Walk around the old lighthouse situated at the top of the bluff and look out at the Atlantic Ocean. This is one of the western-most spots in continental Europe, so the sunsets are amazing! Stay and enjoy the warm afternoons air as it turns into a cool evening breeze.
This beach is the last stop on your two-day tour of Sintra, so take a moment to think about your trip. You traversed lush green mountain paths, traveled through several centuries, and taken a look at wonders both natural and man-made. Take in your last few breaths of sea air, before heading back to the the train station, and the cities that lay beyond that.