
My cousin and I had been dreaming of our own fairytale adventure to Sintra ever since we saw pictures of the Pena Palace. Thus, it was obvious that one of our precious three days in Lisbon should be spent in Sintra. Our driver suggested Cascais as well, and we immediately fell in love!
Our first destination was the Pena Palace. We set out bright and early in order to get there by 9:30 am when it opens (I recommend even getting there a little before that). The entry into Sintra is gorgeous, lush green hills with occasional sightings of the ocean. Up and up the slopes to the Pena Palace, we were thankful we weren’t walking! Our driver dropped us off at the entrance, and arranged a meeting spot in town for anytime in the early afternoon.
We saw a long line snaking out and were daunted initially. However, this line was only for the bus to take you to the palace from the entrance. This is a very short up hill walk, so I recommend you to skip the bus and the line. I also recommend buying tickets only for the outside of the palace.
The Pena Palace is so fun! Three distinct styles all lovely, all in one palace! We spent a wonderful hour and half exploring and taking pictures.

We only bought tickets for the outside (highly recommend you do the same!) so we avoided the awful lines to get inside the palace.
My favorite part was walking along the walls, taking in the simply gorgeous views of Sintra, the Moorish Castle and the Atlantic Ocean.

Once we had our fill of the Palace, we walked down to the town through the gardens of the Moorish Castle. Tip : Turn left out of the Palace gate, then walk down the slope till you see a sign on your right. The walk downhill is so pretty! The old walls with overgrown greenery lends an air of romance, as does the lack of direction. I assure you that you’ll find your way to town though!


The town of Sintra was cute, but extremely crowded. Sintra is no stranger to the tourist circuit, so we didn’t spend much time there. We did stop by Casa Piriquita to eat the famous Sintra travesseiro (puff pastry filled with almond). I love almond, but we agreed that the apple filled one was better!

We chose to go on to Cascais rather than the Quinta da Regaleira since we were daunted by the crowds in Sintra. If you have time, I’ve heard it is an amazing sight though.
Driving to Cascais brought back memories of our drives in California, the Atlantic on this side looking every bit as sparklingly pretty as the Pacific!
We stopped at Boca do Inferno on the way. Boca do Inferno, which translates literally to Hells Mouth, is a chasm in the cliffs through which the waves strike. Breathing in the salty air and listening to the ocean was so beautiful! We didn’t find it very crowded even though it is supposed to be a touristy spot. Definitely make a quick stop though, it’s worth it!
Onward to Cascais and a glass of Vinho Verde! Cascais is a pretty little town on the Portuguese coast; Portugal’s answer to the French Riviera. It has a healthy mix of cute beaches, rugged coastline, and pretty, bougainvillea lined streets.

We went to the rooftop of Cafe Galeria House of Wonders, a vegetarian restaurant. If you decide to go here, walk up to the rooftop terrace and save your table first. Then go downstairs order your food, and order your drinks on the second floor. We didn’t love the food, but the wine on the pretty rooftop was delicious!
Cascais was definitely not as touristy as Sintra, and we could explore the pretty streets to our hearts content. I loved the bougainvillea everywhere!
I hope I can go back and stay in Cascais for a few days next time I’m in Portugal.
We left Cascais around 4:30 pm to head back to Lisbon since we had so much left to explore. Our plan was to stop in Belem, but we decided to skip it since *some* of us fell asleep in the car!
All in all it was a wonderful day trip, full of colorful palaces and sparkling blue ocean views. I cannot wait to explore more of the Portuguese coast (the Algarve perhaps?) and of course, the Azores.
Logistics
How to Get There :
We hired a driver and a car to take us around Sintra and Cascais. With four people, this was a great deal, and so comfortable! For privacy reasons I am not sharing the name and phone number of our driver, but if you contact me for details, I am happy to provide them!
There are trains from Lisbon to Sintra as well. Read more about the train routes and logistics here.
How Long to Spend :
This is totally up to you. Our ‘day’ went from 8:30 – 4:30, but you could tack on Belem for a couple of hours at the end, or spend more time in Sintra to make it a complete day.