We have spent a fair amount of time exploring the many castles that dot Europe’s landscape, so I was pretty excited to add Portugal to the list of countries where we have discovered how the rich and royal once lived. Sintra came highly recommended. The number of people who, upon learning of our trip, spoke of Sintra before Lisbon surprised me. It’s a fairytale, some told us. It’s not to be missed, others agreed. And so it was settled: our first full day in Lisbon would instead be spent in the suburbs.

Trains regularly run between Lisbon and Sintra (about every 20 minutes from Lisbon’s Oriente station), and while we often prefer to travel on our own for day trips, this time I decided to book a small group tour. Honestly, our trip to Lisbon snuck up on me a bit; between holiday parties, work commitments, and traveling to Boston to visit my family, I didn’t have a lot of time to research what to see, how to get around, and where to eat. It seemed more efficient to trust those decisions to the locals.

We traveled with Andre from Portuguese for a Day, a Lisbon native who made it clear from the very start that he loves his home country. Sintra isn’t too far from Lisbon proper, so it took less than an hour before we had arrived, parked, and joined the rapidly forming line for tickets to Pena Palace. December is a pretty quiet month for Portuguese tourism, but you would never know that from the crowd eagerly waiting for the gates to open at 10 AM. I’m sure it was because of the holiday, but I was very grateful Andre was there to purchase our entrance tickets so we could skip some of the waiting!

Pena Palace

Sintra’s Pena Palace, like all good castles, sits on the highest point in the immediate area. While vans are available to shuttle weary tourists from the ticket counters to the palace, there is a beautiful trail that winds up the hill that we walked instead of waiting for a seat in one of the vehicles. Really, I can’t imagine driving to the top; doing so would cheat you from some magnificent views of the castle that you just can’t see properly from a window. The castle shows itself slowly; it peeks out from behind trees and around corners before placing itself on magnificent display as you reach the top of the hill.

After sharing a bit about Pena Palace’s history, Andre left Adam and I to explore at our own pace. Pena Palace dates all the way back to the 15th century, when it was constructed after what was reported to be an apparition of the Virgin Mary. When the 1755 Lisbon earthquake shook the land, the castle was almost completely destroyed. Almost a century later, Prince Ferdinand decided to restore it as the summer home for the royal family, and by 1855 the palace was up and running yet again.

Even if you forget its name, you will remember Pena Palace by its unmistakable color, architecture, and style. From the outside, the bright red and yellow colors date back to Ferdinand’s structural revitalization, though the original paint faded to gray before being restored to its current vibrant tones. Romanticism is reflected everywhere, as are both Moorish and Medieval elements that are as beautiful as they are surprising. Ferdinand preserved as many elements as possible when the castle was rebuilt, including an impressive chapel where bright sunlight cascaded through stained glass windows while we visited. Other elements, like the clock tower, were completely new and designed to royal specifications.

We spent about an hour at Pena Palace, which was just enough for us to see both the inside and outside of the castle; it would have been easy to spend another hour or two if relaxing on the patio or taking a slower walk were on the agenda. But we were excited to catch up with Andre and move on to our second destination: Quinta da Regaleira.

Quinta da Regaleira

Not far from Pena Palace, Quinta da Regaleira is a remarkable estate. You see the enormous palace as you approach it from the road; it is without question a tribute to Romanticism, with ornate details and Gothic and Renaissance architecture. The estate is full of secret enclaves, beautiful gardens, castle-like structures and magical spots to discover at every turn.

From ponds so covered in moss they look like sea foam-colored skating rinks to walking trails lined with lovely plants and flowers, Quinta da Regaleira looks like it’s straight out of a fairytale. Appropriately, at the end of the property stands a castle in its own right, although it never belonged to royalty.

Carvalho Montiero dreamed up his own piece of paradise at the turn of the twentieth century, and the home he built in the form of a castle reflects his eclectic mix of interests. Outside of the castle stands a Catholic chapel adorned with frescas, saints, and, curiously, a few pentagrams.

One of the surprising highlights was the Initiation Well inverted tower, one of two Masonic wells on the property. Yes, that’s right: Masonic symbolism was one of Montiero’s interests, and it is alive and well at Quinta da Regaleira. There is little information available to confirm why the wells were built or how—or if—they were used, though it seems most likely that the well was ceremonial. However, the Initiatiac Well has some remarkable connections to the Masons. Dropping 27 meters, the well was dug far into the ground, with nine landings—or platforms—located at intervals as the staircase winds to its lowest point. Nine serves as a symbolic number (representing levels of hell, purgatory, or paradise depending on the interpretation). On the last level, the Knights Templar cross and a compass decorate the landing. The well is connected to many parts of the estate by a complex system of tunnels.

Given some more time, we would have loved to explore the buildings, tunnels and hidden surprises that are abundant at Quinta da Regaleira, but we made the most of the hour we had. On a day trip to Sintra, an hour is enough time to visit Quinta da Regaleira and see all of the highlights. If we had a few days in Sintra, we would have easily spent another hour or two. But by now it was lunchtime—and we were ready for some Portuguese cuisine!

One of our favorite parts of any tour—and any trip—is the chance to sample typical meals to get a sense of what locals enjoy, so we were excited to sit down for some fresh seafood and cold beer. The restaurant Andre picked was busy (a good sign!) and didn’t have an English menu (a very good sign!), so we let him guide us toward cod cakes and a shredded cod hash with eggs and potatoes. Cod is incredibly popular in Portugal and is the national dish, though interestingly enough it isn’t local to the Portuguese coast. Instead, Portuguese boats fish for it in the waters closer to Iceland and Norway.

We loved our meals (and Andre’s—he kindly let us try the octopus he ordered, which was tender instead of chewy). We washed it all down with Super Bock, one of the two most popular Portuguese beers. Served ice cold, it’s a nice, light beer that pairs perfectly with seafood.

We couldn’t think about eating anything else after such an incredible lunch—until we sat down in a café to try travesseiro, or the “pillows of Sintra.” Many Portuguese towns have signature pastries, and Sintra is no different. With layers of fluffy puff pastry filled with an egg cream and dusted with sugar, these were the best pastries we tried in Portugal. Paired with an espresso, it was a delicious snack.

When we were too full to eat anything more, Andre gave us some time to explore Sintra. While we enjoyed browsing through the many shops, our favorite stop was for Ginjinha, or ginja. Ginjinha is a cherry liqueur that is now somewhat famously served in chocolate cups to tourists for 1 EUR each (we saw them all over the place once we knew what they were), so Adam and I enjoyed an inexpensive digestif. On its own, ginjinha tastes a bit like cough syrup; it’s made from fermented cherries, so it is very strong. Paired with chocolate, it has a nice, smooth taste and is perfect after a meal. We didn’t want to buy a whole bottle, but it was absolutely worth spending a Euro to try it.

Cabo da Roca

With our time in Sintra complete, our next stop was a favorite of mine—Cabo da Roca, or continental Europe’s westernmost point. I love visiting extremes; we have stood at the Cape of Good Hope (Africa’s southernmost point), and we have visited Þingvellir National Park in Iceland where we saw the tectonic divide between North America and Europe, so this was a fun stop for me.

We wrote about a map a while back that illustrated what a person is looking toward when they stand on the coast of a country and look out across the ocean; Portugal is on the same latitude line as our home in the Washington, DC area, so we spent a few extra seconds gazing toward our friends and family thousands of miles west of us before heading back to the van for our final stop.

As the sun began to set along the beach, we made our way into Cascais, a coastal town famous for being home to many of Portugal’s rich and famous. Cascais is absolutely charming. With lots of shops, plazas, and restaurants lining its cobblestone streets, it’s a great place to visit; it’s popular with domestic and foreign tourists alike. We didn’t have a whole lot of time there, but spending some quiet time looking out at the fishing boats was a relaxing end to a very full day.

Not long after leaving Cascais we were back in Lisbon. We started our day knowing that everyone who visited Sintra seemed to love it, and we found that to be true for us as well. From castles to gardens to great food, we had an incredible day. A big part of that was because of Andre; while we could have found our way to and around Sintra on our own, I am so glad we spent our day with Andre instead. His knowledge of and passion for Portugal was contagious, and so much of what we learned from him was reflected throughout other tours and experiences we had during the week. He was an amazing guide who made us feel more like friends than customers.

Lisbon Hotels

Ready to book a room for your own trip to Sintra? Lisbon has plenty of options and it’s a great place to start your vacation. Here are some hotel deals to consider:
 


Booking.com

Visit Lisbon and Sintra!

Sintra is a popular day trip from Lisbon, and for good reason. If Lisbon is on your radar, make sure to save a day or two for Sintra—as soon as you see the castles on the horizon, you will be glad you did!

 

Related Posts

Are you considering a trip to Portugal? Here are a few more posts to help you plan the perfect vacation!

* From time to time, our travels are directly impacted by a service or company. In this case, we booked a day tour with Portuguese for a Day, and this post includes our candid review of our experience. We selected Portuguese for a Day based on our own research and travel needs; we were not offered and did not receive compensation of any kind from them or any other party in exchange for our review. We may receive a small commission on tours booked using our exclusive code Portugueseforaday_RoadUnraveled on the Portuguese for a Day website.