[Cascais / Sintra, Portugal, May 16, 2025]

A daytrip to Sintra tops the wishlist of many visitors to Lisbon. Its proximity to the capital, the magnificent architecture of its palaces and castles, and its status as a UNESCO World Heritage site all contribute to the draw. I would normally do a side trip like this on my own, but Sintra presented some unique challenges. Due to the palaces’ popularity, a timed entry ticket was required, but one could still wait in line for their time slot. In addition, the Sintra train station was still a little ways away from town. I’d read that the buses that connect the train station to the city can get crowded, leading to more lines just to get on.

All this sounded like more trouble than I wanted to deal with and I booked a small group guided tour on Viator. The tour included a couple of other sites outside Lisbon, which added to the appeal.

The group met bright and early, at 8 am, at Praça da Figueira, which was a mere 3-minute walk from my hotel. We climbed into the van and headed for our first stop.

Cascais is a lovely seaside town just 30 minutes from Lisbon. King Luis I made the town popular when he and his family established a summer residence there in the 1870s. The nobility followed, and today Cascais is one of the most expensive places to live in Portugal. An influx of royals from all over Europe during WWII gave the coast its nickname, “coast of Kings.” Even members of the last Bulgarian royal family made their home there. We only had a short time to explore, but I managed to find a small beach and walked around the city center.

Our next stop was just a little bit up the coast. Cabo da Roca is the westernmost point in continental Europe. The cape is within the Sintra-Cascais Natural Park, just southwest of Sintra. Its coordinates are inscribed on a stone plaque at the monument at the site.

The lighthouse, which began operating in 1772, was, sadly, off limits to visitors. Despite the relatively early hour, it was quite busy.

Finally, we started making our way to Sintra. We found a parking spot for the van fairly easily, although I had to admire the skill required to fit it into the tight space. We noticed quite a few banners hanging from various fences and balconies. They represent a protest by the locals against the Sintra City Council, which, in their view, has not done enough to properly manage the influx of visitors. Each entry ticket includes a fee that goes to the city council. It adds up to quite a bit of money, but it was obvious even to us that very little of that has gone towards more effectively managing the huge number of people that descend to the small town every day.

From there, it was a short walk to the city center, which was bustling with people. The National Palace of Sintra flanked the square. It is a mix of Moorish and Manueline styles. I loved its distinctive conical towers are actually chimneys that vent the kitchen.

We also passed the Lawrences Hotel, the oldest on the Iberian peninsula. It opened in 1764.

The first palace we visited in Sintra was Quinta da Regaleira. The land originally belonged to the Viscountess of Regaleira, a family of wealthy merchants from Porto. They sold it to Antonio Augusto Calvaho Monteiro, who built the current estate. The property changed hands several times. However, its inclusion in Sintra’s Cultural Landascape, a UNESCO World Heritage site, made it impossible for its last owners, the Japanese Aoki Corporation, to make the renovations it wanted. In 1997, the SIntra City Council acquired the property and it opened to the public in the early 2000s.

A large part of the estate is taken up by lakes, gardens, grottos and various whimsical buildings.

The most popular feature is the Initiation Well, which is more akin to an inverted tower. It never actually held water and is believed to have been used for ceremonial purposes. A large spiral stair case descends nine levels to the bottom, where a series of tunnels lead back out. The nine flights of stairs could be linked to the Knights Templar, which had nine founders, or they might also symbolize the 9 levels of Hell from Dantes’ Inferno – nobody knows for sure. The Initiation Well is so popular, it had its own line to enter! Luckily, we only waited about 15 minutes but our guide said the line can take as long as 45 minutes! Once in the well, a staff member kept people moving, which was absolutely necessary – otherwise the narrow space would become bottlenecked by everyone stopping for photos!

A Roman Catholic chapel stands in front of the palace’s main façade. Frescoes, stained glass windows and lavish stuccoes decorate the interior. Despite its relatively small size, the chapel has several floors.

Only the main floor of the palace itself was open to the public. I loved the woodwork on the ceiling. Most of the furniture is now gone, but it allowed us to marvel at the architecture and decorative elements in each room.

And now it was time for lunch! Most of the people on my tour ducked into a small restaurant that our guide recommended. But it didn’t have outdoor space or views, so I decided to strike out on my own. I headed up the hill, hoping to leave most of the crowds behind. I stumbled upon Dona Maria, and I couldn’t resist its large patio overlooking the Moorish National Palace of Sintra. The octopus was delicious!

Then, I headed to Piriquita, the oldest pastry shop in Sintra. Established in 1862, it’s most famous for the Travesseiro – filo pastry filled with sweet, eggy almond cream. I also got a quiejada – sort of like a pasteis de nata, and chocolate salami. I needed all this energy for the uphill walk to our next stop – the colorful Pena Palace.

In the 12th century, what is Pena Palace today was just a chapel dedicated to the Order of Our Lady of Pena. The chapel still stands and is easily recognizable by its red color. Later on, King Manuel I ordered the construction of a monastery, which was destroyed in the 1755 earthquake. In the early 19th century, following the abolition of religions orders in Portugal, the site was abandoned. Enter King-Consort Ferdinand II, who purchased the site with his own money in 1836. A man of great education and appreciation for the arts, King Ferdinand quickly abandoned his original idea, which was to simply restore what was there, and ended up commissioning the masterpiece of a palace that stands there today. He drew inspiration from Manueline and Moorish architecture, but also incorporated classic medieval fortress elements such as lookout towers and even a drawbridge.

Shortly after Portugal became a republic in 1910, the palace became a national monument and was eventually included in the Sintra Cultural Landscape UNESCO World Heritage Site. Our ticket included the grounds only and not the palace itself, but that was more than enough. There is a whole separate ticket with timed entry for the interior, but I don’t feel like I missed anything by not going inside.

We left Sintra around 5 pm and got back to Lisbon a little after 6 pm. Because there was a lot of traffic, our guide dropped us off at Praca Marques de Pombal, the square dedicated to the guy who was instrumental in rebuilding Lisbon after the 1755 earthquake. From there, it was a gorgeous 20 minute walk downhill on Avenida de Liberdade to my hotel. It was a wonderful way to end my two weeks in Portugal. What an amazing trip!