Pick Two: Palaces in Sintra

We didn’t do Regalaira because our local guide said it wasn’t worth waiting in the huge line. Probably Monserrate, it wasn’t crowded and the gardens were beautiful.

You will get various opinions on which palace to go to. for me, I actually loved Quinta da Regaleira for the amazing staircase going down into the deep well and walking through the cave like setting with dripping water and nice little grottoes. I would definitely consider Quinta da Regaleira as a first or second choice Next to Peña Palace

ETA: Also, the Quinta visit was nice because we remained out of the heat. We visited in early October 2023 and it was still very warm in Portugal. The coolness of the caves was a very nice escape from the heat.

The Moorish Castle is a ruin but it was my favourite between it and Pena. We didn't have time to visit the other. It's a beautiful walk through a lush forest to get to the castle and then you can walk the walls to the top for some killer views.

Thanks for your feedback although it didn't help me narrow it down! haha!

Thanks for your feedback although it didn't help me narrow it down!
haha!

Probably the correct answer is that you'll likely enjoy whatever you choose. No sense on stressing on what you might have seen.

My opinion seems to be different than 90% (100%?) of people who visit Sintra. I was not interested in or impressed by Pena Palace. There were many, many people there, and it was a huge slow-moving line through the rooms. Keep in mind, also, that this palace was built / reconstructed in the mid-1800s, so it's not very old (in terms of European castles). It was built during the Romantic period, to be evocative of older (and idealized) structures.

I loved visiting the National Palace, which is in Sintra. There were few people, and each room had different and marvelous tiled walls. It's much older than the Pena Palace, which I also appreciate; some portions of this Palace are older than others.

The Moorish castle was ruinous and somewhat interesting.

Quinta de Regaliera was built as a (large) folly, and was fun, though when we were there it was also mobbed by people.

With private tour you can pick your own spots

Moors castle is ruins and require a climb up.
Ground tickets of Pena palace is flexible and lets you see all colorful terraces that matters.
(do buy shuttle bus ticket from entrance to palace to save energy - offer to stand if it helps you get into a full bus and not wait for the next one - it is only 7 minutes ride)
QR is a unique park with well and caves
Monserrate is a beautiful park that is much less crowded.

You might be able to do three but if you can do only two then Pana and QR will be my choice.

We hired a private guide when we went to Sintra and we saw the National Palace, Quinta da Regaleira , the Moorish Castle and Pena Palace including the interiors all in 1 day. As the above poster shared , the Moorish Castle is in ruins and can be challenging to negotiate. In looking online for day trips to Sintra, a number of them do include Cascais. We did not go there as we didn't have the time. One option could be to skip going to Cascais and then you could spend some more time in Sintra. For my 2 picks I would choose the National Palace and Pena Palace. If you choose to stay in Sintra, then I would add Quinta da Regaleira.

Thank you all for your feedback. If we do Pena, it'll probably just be the exterior/gardens.

And I think you're right--we'll enjoy whichever ones we get to see!

If I could only choose 2, I guess I would say Regaleira and Monserrate, but wow, what a tough decision. I didn’t go inside PP, just enjoyed the gardens and the terrace. Moorish was different than the others and I loved it as well, but Monserrate had a beautiful palace to look at (although it isn’t so big, it had stunning detail) as well as lovely gardens with a few hidden treasures, it was easy to get a Bolt out and back.

I just made a post called "Practical tips learned from our 5-day stay in Lisbon", which included our experience in Sintra. We went there on 2 separate days and visited Pena, Monserrate, Moorish Castle, and Regaleira. If I have to pick 2, I would pick Monserrate and Regaleira. We are like you -- in our 50s and love history, so I think you would like those 2 places the best.

Moorish Castle has nothing for you to read. It's essentially a hike up to the top of the mountain with some stone walls. I cannot speak to the inside of Pena as we didn't go in. In Monserrate, we enjoyed reading the placards of every room and watching the video interview of the son of the caretaker who spent his childhood on the estate. And it has a very extensive garden that is like a maze. QR obviously has the famous Initiation Well, but be sure to visit Labyrinth Groto and a few other interesting sites on the grounds. (The building itself in Regaleira is not as interesting.)

It woud take an hour or two to just walk around the grounds of each place without lingering, but in order to truly enjoy a place or read about its history, being able to linger is a must. We spent 3 hours each at Monserrate and Regaleira, but still felt that we could have used more time at each place.