Just a short trip from the bustling capital of Lisbon and you’ve entered the fairytale city of Sintra, Portugal.  A varied history of conquests has led this region to collect a motley assortment of reminders from the past, offering an intriguing blend of eras everywhere you turn; Renaissance, North African,  Gothic, Roman…the list goes on.  A quick look around and it’s no wonder that man from all over the world waged war for this land. While the pastel hued houses of Sintra highlight the desire to live here, the most powerful evidence can be found by tracing your way up the lush and green rolling hills that pan out from the center of town. Up there in the sky? Magnificent hints of royalty; in the form of two majestic castles, both spinning a different tale of this very peculiar, yet fascinating city.

SKINNY:

• If you are in Lisbon for 3 days or more, DO visit Sintra.
• Take the train, it’s easy and inexpensive.
• Head to Sintra early in the morning to avoid the influx of tourists.
• Castle prices are a bit steep, so research which ticket to buy before you visit.
• Food options are flooded with many not-so-tasty, non-wallet-friendly  options. Research where to grub before you go!

ARRIVE:

If you plan to only visit the city of Sintra and surrounding castles, don’t drive! The winding roads of Lisbon and limited parking in Sintra is cause for a headache. Plus, the train is SO. EASY.

The Lisbon to Sintra train departs from the Rossio Train Station which is located in the popular neighborhood of Baixa. The station is connected to the green metro line if you aren’t staying within walking distance.

Since it’s a commuter route, there are many departures per day. I recommend taking an early one so you can explore more! If you haven’t used Lisbon’s “Viva Viagem” ticket system yet, I suggest you get to the station conservatively early for your train. Not only to beat the lines, but to carve out some time to fight with the ticket machines. The 24 hour ticket isn’t valid for Sintra, so you have to buy an individual return ticket at about 5 euros. The ride is about 40 minutes.

When you arrive, the historic town center is just a 1.5km walk from the station. There are signs that show you the way if you aren’t exploring during peak season (when you can just follow the flock). The walk gives you a feel for this quaint, hilly city and gives you some stellar views into the distance.

For the other sights below, we originally planned to walk to all of them – work off the Nati de Pastais. We did stroll by foot to Quinta da Regaleira, but learned that the castles high up on the hills looked way closer than actuality.

We realized this only after we started making the winding trek up. Luckily, we were able to flag down a pedicab early on, but I’m not so sure this is common. Most people take one from the town center. The ride charges 5 euros for each person. Oh AND they drive like bandits, which is good fun on the way up, and especially on the way down! After you explore, there are many pedicabs waiting near the entrance to take you back down.

A more economical option for getting to and from the hotspots is bus # 434. My source is personal experience since our pedicab driver almost turned us into Portuguese pancakes after coming face to face with this bus.

STAY:

Most people visit Sintra while staying in Lisbon. I really liked the area we chose to stay in; Barrio Alto. It’s a young neighborhood with loads of up-and-coming charm. Just beware of possible street noise from the exuberant nightlife in this area.

The bad news? I took a chance on a fairly new Airbnb listing and regretted it the moment we walked in. Not because of the vibe; it was super modern, spacious, and had a lot of character. The negative aspect was in the air…literally. They had an AWFUL plumbing issue that was so pungent that we tried switching, but we didn’t want to spend our time in Portugal researching accommodations. Instead, we were partially refunded AND given a sizeable Airbnb credit. So, word to the wise? be careful when you play risky on Airbnb and if your gamble goes sour, be sure to ask for what you deserve!

From more recent reviews, it looks like they’ve remedied the issue, so feel free to check it out: https://www.airbnb.com/rooms/14191661

EXPLORE:

Quinta da Regaleira

By far, this was my favorite stop in Sintra! The Quinta da Regaleira is a World Heritage protected palace and grounds, straight out of a Renaissance-inspired fantasy world.

This massive estate cycled through many owners in it’s lifetime, but began it’s mystical transformation after Antonio Augusto Carvalho Monteiro bought the property. This wealthy Portuguese entomologist dreamed of living in a mysterious and magical place. And when your nickname is Monteiro the Millionaire, money can buy dreams, so he hired a renowned Italian opera set designer and architect to do just that.

To create this eclectic masterpiece; they combined Roman, Moorish, Gothic, Renaissance, and Manueline styles. As if this isn’t eclectic or bizarre enough, one can find symbolic carvings associated with Masonry, the Knights Templar, and Rosicrucians throughout.

As for the indoors, visitors can roam through the palace and peak into the chapel. Both buildings are windows into the past; sporting intricate architecture and decor from faraway eras. Proof? The Gothic exterior of the palace is adorned with pinnacles and Gargoyles. As you make your way through the interior rooms, you’ll find a billiards room and a Baroque fireplace that has more detail than your Senior year thesis.

However, the most incredible part of this UNESCO site are the surrounding grounds. Remember that movie The Secret Garden?  If you don’t, you missed out on a quality flick and should rent it as soon as possible. More importantly, the gardens of Quinta da Regaleira makes the main character’s garden look like a sad flower box. Anyway, go ahead and get lost here as you explore the greenery, grottos, and lakes.

And don’t forget to dip into the underground tunnel systems and spiraling wells. As if that’s not mysterious in and of itself, rumor has it that these wells were used for secretive initiation rites. It is believed that the Initiation Well’s nine platforms represent the nine circles of Hell, sections of Purgatory, and skies of Paradise from the Divine Comedy. As for the other well, theorists have speculated that it’s design is tied to Masonic Principles which is certainly strengthened by the ground’s image of the Knights Templar. If you’ve never gone down an Illuminati rabbit hole, this is your chance!

Park and National Palace of Pena

The fairytale of this region continues with this vibrantly colored castle sitting high up in the Sintra hills. Aside from Germany’s Neuschwanstein Castle, I never imagined that an authentic palace would remind me of a Disney theme park…I figured it was always the other way around. So, it comes to no surprise that King Ferdinand II’s goal was to rival the famed Bavarian castle. He was in awe at the sweeping views from this high altitude location and wished to design a palace that resembled an opera.

During your visit, you’ll see that his designer stuck to those exact blueprints. He capitalized on the incredibly stunning 360 degree views with terraces that wrap all around a vibrantly flamboyant structure.

Ticket prices are steep, so we opted for the terraces and grounds package, missing out on a tour of the inside. Others have marveled at the interior, so if you can swing it, go for it. However, if you are pressed for time or money, do not miss out on the terrace views…they are breathtaking. We even had the challenge of a foggy day, so I can’t imagine the panorama with a clear sky.

The surrounding grounds are interesting to explore, lakes and structures set against the backdrop of a thick forest. However, after the whimsical land of Quinta da Regailera, it may be easy for those who tire easily to become unimpressed.

Centro Historico de Sintra

This is your typical preserved “old town”, but feels more like a slice due to it’s size. A handful of windy, cobblestone streets filled to the brim with cafes and shops. Since it is the center of town and it is rather small, you might feel a bit suffocated by the density of souvenir-pushing.

For Next Time

Castle of the Moors

We caught a glimpse of The Moors Castle (Castelo dos Mouros) from a few different angles; peering up from city level, passing the entrance on a fast buggy, and an aerial view from Pena Palace. Due to time, as well as the expense, we didn’t officially visit (although there is a combo deal if bundled with Pena Palace).

This castle has an interesting history and is situated in an amazing hill-top location. It was built in 9th century by North African Moors, but was neglected for quite some time after the Christian take-over of Portugal. The mere history of North African conquest is fascinating in and of itself! If you have the time or cash, let me know how it went!

Praia da Ursa

Portugal’s beaches are breathtaking, so it’s always sad to miss an opportunity to gasp for air while marveling at one of them. Luckily, we were headed to Algarve the next day, so this beach didn’t make the cut.

If you do decide to visit…Praia de Ursa is NOT walking distance from the main attractions in Sintra (and I consider 10 miles walking distance), so it’s a bit more involved to get to if you don’t have your own transportation. If you do have a car, go! I’ve heard positive things.

GRUB:

We messed up on our choice and I’m not a huge fan of knocking places, so choose wisely for brunch/lunch before you head out…there are some interesting looking places!