A Magical Afternoon in Sintra

After a memorable introduction to Lisbon’s cuisine and city sights, it was time for us to escape out to Sintra Natural Park, what I can best describe as a magical fantasyland. A suburb 25 kilometers to the west of Lisbon, Sintra is located in the pine covered hills of Serra de Sintra and home to three royal palaces among other grand buildings and scenic vistas as well as the westernmost point of continental Europe, Cabo da Roca.

After the bit of rain we had had the day before, we joyfully woke up to clearer skies and left the hotel in search of this mystical land. After a quick detour of wandering the several blocks of stalls of the weekend outdoor market that line Avenida da Liberdade (and scoring a €5 decanter for our bar cart at home!), we hopped aboard the train at Rossio station bound for Sintra. Forty five minutes later we arrived at Sintra station, about 1km east of the historic centre, and opted for the tourist bus that saves the steep 45 minute climb up hill to the main sites, though the trail looked quite shady and picturesque.

Perhaps next time, as we quickly realized that a day trip out to Sintra would not be nearly enough time to see all the sights. We decided to narrow down our choices and settled on the two sights that would allow us to be big kids for the day, climbing towers and exploring hidden passageways; the Moorish Castle and the Quinta da Regaleira.

The Moorish Castle or the Castelo dos Mouros, was a military fort built around the 10th century by the Muslim population that occupied the Iberian peninsula. With panoramic views out to the ocean it acted as a control tower for the Atlantic coast and provided expansive views of encroaching enemies from the North. The castle’s Muslim rule ended in 1147 AD following the conquest of Lisbon by King Afonso Henriques and in 1839 King Ferdinand II initiated a campaign to restore and renovate the castle and its surroundings in the free, romantic style of the 19th century. From the castle walls one can see the Pena Palace, Quinta da Regaleira, Monserrate Palace, the National Palace, and Sintra Village.

We had so much fun walking along the narrow castle ramparts, exploring the many winding paths, and clambering up steep tower staircases to be met by the most amazing views. There is even a canopy zip line rope course that you can ride to admire the castle from above. After taking the bus back down to the historic centre and enjoying a leisurely rooftop terrace lunch at Cafe Paris of the most tender, delicious, melt in your mouth steak we walked through town toward the Quinta da Regaleira estate, a magical playground for both kids and adults.

Built in the late 1600s the estate changed hands various times and underwent several transformations, gaining its name of Quinta da Torre da Regaleira in 1840 after being bought as a summer retreat by the Baroness da Regaleira. Built in the neo-Manueline style, the four hectare estate was the summer residence of the Carvalho Monteiro family in the late 1800s who transformed the place to its present day form between 1898 and 1912. The design of the estate was inspired by the owner’s mystic ideologies and there are hidden references to the Knights Templar, the Masons, and dark alchemy throughout the grounds. Exploring the gardens, grottoes, and tunnels that encompass the estate quickly became the most enjoyable and memorable afternoon of our trip thus far!




So many towers and grottos and winding staircases to explore! At the Terrace of the Celestial Worlds we happened upon a historical re-enactment with music and dancing and a bit of dialogue. Although it was in Portuguese, so we were a bit clueless as to what the context of the re-enactment was.


Dan’s favorite discovery was the four underground passageways that one can take from grottoes at the bottom of the estate up to the Initiatic Well. Some portions of the tunnels were lit but others were pitch black. Thank goodness for the flashlight app on the iPhone!


From the Terrace of the Celestial Worlds we had walked over to the Portal of the Guardians, a pavilion flanked by two towers, under which hides one of the hidden walkways to the Initiatic Well. We stumbled along in the dark for a dozen meters or so before the tunnel opened up to the spiral stairway of the “subterranean tower” that sinks 27 meters into the ground. Such a fun discovery! Dan and I were grinning ear to ear like two big kids.

The well symbolizes the initiation ceremony for the Knights Templar and is meant to make the relation between Heaven and Earth deeply felt. Not sure I felt that strong of a connection but it is definitely an awe-inspiring place! We wound our way all the way up to the top and then down to the bottom of the staircase and then explored the three other underground passageways before making our way back out to the harsh daylight.


The estate comprises four hectares of beautiful gardens and winding pathways that just seemed to keep going up and up from where they started at the bottom of the estate. There weren’t too many other visitors that afternoon and we often found ourselves peacefully alone in exploring the far reaching corners of this mystical place. I imagine the groundskeepers have quite a task at the end of the day searching for straggling tourists come closing time.


After a thrilling day of exploring the magical fantasyland of Sintra, we capped off the night with drinks with a view at Tivoli Lisboa hotel’s rooftop Skybar. I wonder if I will have dreams of Peter Pan and the Lost Boys tonight…


After waking up to bright sunny skies, Dan and I had a couple of hours left in Lisbon before our afternoon train south to Lagos, so we hitched a ride on the iconic yellow trams that trundle people across the city and up and down Lisbon’s seven hills. After catching the #28 tram at Praca Luis Camoes we went for a scenic but harrowing loop through the Bairro Alto neighborhood and back.

The trams really challenge your balance as they not only rock you side to side but forward and backward, as they make the climbs up and down the hills. There are a dozen seats or so inside the tram but they are often packed to standing room only and it wasn’t an uncommon sight to see one or two people stumble across the tram and bump into one another as the tram lurched up and down. It was a classic Lisbon experience but I couldn’t imagine having to commute like that everyday. I appreciate the London tubes with their flat routes, even when they are packed and uncomfortably hot at rush hour, much more thats for sure!


Lisbon’s spirited vibe paired with its long, rich history (the port city predates Rome by 400 years!) captivated us. Regrettably we didn’t plan enough days to venture out and explore all the magnificent sights and museums such as the Castelo Sao Jorge that we had wanted to and are already dreaming of our return holiday in the future.

After a whirlwind three days in Lisbon, it was time for us to head to the train station and catch our southbound train for the final leg of our trip and our final Portugal destination, the sandy beaches and rocky coves of the Algarve!

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  1. What a wonderful time you guys had in Lisbon, Flo and I also visited Lagos and Algarve on our trip. But I ‘ll bet we didn’t see everything you guys will explore when you get there. Keep having fun on this trip. I am enjoying reading about, and seeing all that we missed.

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