The Best Way to Tour Sintra and the Cascais

Sintra, Portugal is a place I had heard a lot about – a “must visit” if you are spending time in Lisbon. However, aside from the infamously colourful Pena Palace, I didn’t know a whole lot about Sintra and the surrounding Cascais region.

For many, Sintra is just a daytrip from Lisbon to visit the popular castles. And while that is a totally reasonable option, once I began to research more about the more largely unexplored Sintra and Cascais region, I knew settling on a day trip to bump elbows with other tourists at Pena Palace and head back to Lisbon was not what I envisioned for my time here.

Once I began exploring my options, there was only one tour company offered everything I was looking for: Greenwalk Tours.


Greenwalk Tours is a small private tour company, local to the Sintra and Cascais region, that specializes in nature, history, and cultural sightseeing. They operate a wide variety of tours to cater to many different interests, and are known for their intimate off-the-beaten path approach to exploring Portugal. The tours are provided by seasoned tour guides, who have studied geography in school, and who pride themselves on providing exciting and educationally accurate tours.

Greenwalk Tours offers a wide variety of tours, including hiking, biking, and Jeep tours. In the interest of time and seeing as much as possible, we opted for the most popular “Romantic Views Jeep Tour,” which includes the perfect blend of both popular sights and beautiful natural sights that can only be accessed by off-road paths.


After looking into the process of getting to Sintra, we opted to stay locally at Chalet Saudade the night before our tour in order to avoid the busy train crowds, which I’ve heard can get quite chaotic heading from Lisbon to Sintra in the morning.

See Also: The Chicest Boutique Hotel in Lisbon [with a rooftop pool!]

Our day started bright and early with the perfect breakfast at Cafe Saudade, which was right across the street from the Greenwalk Tours head office. We then proceeded to go meet our guide João, and headed toward the castles to get a head start on the crowds.

Pena Palace & Moorish Castle

We drove up toward the castle and parked at a secondary entrance, away from the main entrance [and crowds]. The grounds surrounding Pena Palace deserve as much credit as the castle itself, and contain greenery that has been imported from countries all over the world. João told us about the origins of the various plants, and why they were selected. We learned about the exciting history of the gardens and the two castles – Pena Palace and Moorish Castle. João was very engaging, and kept the content exciting.

Even at 9:30am, Pena Palace was busy. But we still managed to beat most of the crowds, and opted not to take the tour inside in palace as the line was already quite long. I can’t begin to describe how critical it was to have a tour guide during this time, as we were able to avoid the busy bus crowds, park away from the main entrance, and walk through the beautiful, and largely desolate, castle grounds on our way to the castles.

The Sintra-Cascais Coastline

Just as the castles started to get really busy, we jumped back into our car and headed for the coast. Along the way, we drove through narrow streets with some of the most lush greenery I have ever seen. This was a general theme through our time driving through various regions of Portugal. The whole country is SO HILLY and SO GREEN.

Sintra Views

We rolled through small, beautifully maintained villages along the way, and learned about life for locals in the villages. From there, reached the coast, where we explored a couple of the local beaches, including Azenhas do Mar and Praia Grande. Praia Grande is a very popular beach to visit in the summer months, and is known to get very busy. So busy, in fact, that locals have been known to sleep on the beach the night before to secure their spots in the morning. It was very clear how much Portuguese locals love the beach considering it was barely 20 degrees in April, and there were locals swimming in the water.

Next, we were off to the most remote location of our adventure. The only way to get there: a winding off-road path. Thank goodness for 4×4! Here, we reached my favourite coastal location with the most incredible views of the ocean. The sky was the perfect shade of blue, the clouds were so fluffy, and the only other people in sight were João and Sebastian. It was such a special moment of complete serenity.

Our final coastal stop was the most western point in Europe: Cabo da Roca. It was also only spot along out coastal adventure that we ran into other tourists – and there were a lot of them. Even still, it felt pretty cool to stand on the most western edge of the continent, admiring the views of the Atlantic.

Convent of the Capuchos

After we finished exploring part of Portugal’s breathtaking coastline, we headed inland, where to drove through as maze of greenery, and stops at a couple more historical landmarks. The final of these landmarks, a 500 year old convent called Convent of the Capuchos was a huge highlight.

Joao told us all about the life of the monks who inhabited this convent over 500 years ago, and we toured the very tight living quarters [these monks must have been SO tiny]. We saw everything from their well-preserved kitchen, to their sleeping quarters, and their chapel. There were, again, no other visitors around, and we walk around and explored this incredible historical treasure.


Because they are the best! But seriously, I can’t imagine a better tour company. This is a team of pure professionals. They love Sintra, and are committed to showing visitors the REAL Sintra.

And they are affordable. For 65 euros per person [for a group of two; price per person goes down with larger groups], you can spend an entire day cruising around Sintra & the Cascais.

Plus, they cater to your interests. Do you have something you are dying to see? They will alter the itinerary to suit your interests. And they provide the best recommendations.

I truly can’t say enough about this experience; It was easily one of the top highlights of our time in Portugal.

If you’re currently planning your trip to Sintra and the Cascais, click here to see all the amazing tour packages offered my Greenwalk Tours. And be prepared to make the best memories.


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