One of the most popular day trips from Lisbon is to the lovely little town of Sintra. We had been planning to visit Sintra on our second to last full day in Lisbon but Dan still wasn’t feeling great. Luckily we ended up pushing it back to our last full day – it turned out there was a nation-wide train strike on the day we originally planned for. (Thank you Google Translate for revealing that ‘greve’ means strike. That would turn out to be an important word to know for the rest of our time in Portugal.)

While the town of Sintra itself is charming, the main attractions are the many castles and palaces perched in the surrounding hillsides. Everything I had read said that in order to see multiple castles in one day we needed to get there early. We hopped on a train from Lisbon and about an hour later arrived at the Sintra station. From there we caught the tourist bus which does a little loop from town to the most popular sites. Even though we arrived late morning the bus was already packed and we had to stand for the winding ride up the mountain to our first stop, Pena Palace.

A little dizzy, we hopped off the bus and joined the snaking line to purchase our tickets. From there it was another 15 minute hike up the hill through the estate’s gardens to the palace itself. Once inside we joined yet another line to wind our way through the castle’s interior.

Despite being herded about as part of a massive crowd we couldn’t help but enjoy this gorgeous building. The architecture is an eccentric mix of styles and the brilliant colors pop from the lush green hillside. The views from the many courtyards and balconies were stunning.

We had brought a picnic lunch since we didn’t want to waste time and money trying to find food once we had gotten to the palaces. This turned out to be a good call because we got the opportunity to walk through the sprawling Pena Park and find a peaceful spot to sit and enjoy our picnic. From there we walked a little ways down the hill to castle number 2: the old Moorish Castle built in the 8th and 9th centuries.

The Moorish Castle is less intact than Pena Palace but it looks more like the stereotypical castle you see in children’s books. The walk along the walls offered more amazing views, both down the mountain towards the sea and back up towards Pena Palace.

From there we got back on the tourist bus to catch a ride down the mountain and in to town. Insider tip: the bus going this direction stops at the Moorish Castle first so you have a much better chance of getting a spot there than you do at Pena Palace just a few meters away. I was anxiously checking my watch as we made our way down but we ended up having plenty of time to see one more site that day. On the advice of some Lisbonites we had met back in Porto we decided to make Quinta da Regaleira our last stop.

Quinta da Regaleira is only about a 15 minute walk from Sintra town. The palace building itself is a gorgeous home, filled with fanciful architectural details.

However, the real highlight here was wandering around the greater estate and finding all the strange features hidden in the landscape. The most bizarre of these was probably the Initiation Well: described as an ‘inverted tower’ with a spiral staircase leading several stories down into the earth.

The grounds surrounding the estate also feature a small aquarium, numerous grottoes and an ornate chapel. Despite being exhausted from all the walking we had done that day it was totally worth it to explore this incredibly unique and beautiful property.

After that we wandered back to town for dinner before catching the train back to Lisbon. The trains run very frequently (when they aren’t striking) and it was a very easy and enjoyable trip to do via public transit.