Discover Sintra and Cascais in 3 Days

Day 1

A Tour of Sintra, Portugal

Our tour of Sintra begins in the heart of town with a sample of the local pastries. From there, we’ll take you on a journey through Sintra’s main attractions, including the infamous Pena Palace. It’s only a few miles from Lisbon, but this resort town is nothing like the capital, as you’ll find out the minute you step off the train station and spot the green hills of Sintra.

Things To Do in Sintra - Morning

After spending three days in Lisbon, I was ready to hop on a train and discover a different town. Following Iberian Escapes suggestion, I headed to Sintra, a romantic village located a few miles away from Lisbon.

I got the train from Rossio and, within 40 minutes, I was in the heart of Sintra. While I was excited to explore the town, I had to drop my things at the hotel first, so I got in the first taxi I saw and made my way to the Penha Longa Resort. Set amidst the Sintra mountains, this resort immediately stood out when I was looking for a place to stay in Sintra. Besides all the luxury amenities available, it was the surrounding gardens and the stunning views of Sintra that led me to choose this hotel above all others.

Once I got my bedroom sorted, I headed downstairs to meet the hotel concierge and requested the keys for my rental car. I’ll be driving it for the next few weeks as I continue my Portugal Tour. But first, I’m sticking around Sintra and seeing what this town has to offer.

With my new car, I drove back to the centre of Sintra to visit the main attractions. I started my tour at Piriquita, a café famous for its traditional pastries—queijadas and travesseiros. The first one has the shape of a tart, and it’s made with cheese, eggs, milk and sugar, while travesseiros are made with puff pastry and filled with almond cream. Just like with Pastéis de Belém, you can eat them inside the café or take it as a snack for later.

When I arrived, there were a few tables inside, so I decided to stay and savour these delicious sweets with a cup of coffee.

Once I finished eating, I walked to the Sintra National Palace. Its tall conical chimneys were one of the first things I spotted when I arrived in Sintra. Dating back to the 9th century, it remains one of the best well-kept medieval palaces in the world, despite its modern appearance. In the 16th century, King Manuel I decided to revamp the whole building, creating new rooms like Sala dos Brasões, which features the coat of arms of Portuguese nobility. This room is the highlight of the palace, not only because of the coat of arms in the ceiling but also for its impressive collection of tile panels covering the walls from top to bottom.

My next stop was Quinta da Regaleira. I lost track of time while I was inside, as there were so many things to do. It’s hard to imagine this mystical place was once a private estate.

As well as a palace and a chapel, you’ll find grottoes, tunnels and water fountains all over the park. Of course, I couldn’t miss the spiral staircase leading down to the well, and the stepping stones across the water, the two main features of Quinta da Regaleira.

When I finally checked my watch, it was coming up to lunchtime, so I got in the car and drove to INcomum. Set near Sintra’s train station, INcomum is a modern Portuguese restaurant run by Chef Luís Santos. They had a special lunch menu, so I decided to get that, which included a delicious shrimp risotto.

Afternoon

In the afternoon I visited two more attractions: Castelo dos Mouros and the Pena Palace.

Standing on a hilltop, the castle offers spectacular views over the Sintra Mountains. Walking along the ramparts, I could see the whole town, but I had my eyes set across the hill where the Pena Palace stood. I couldn’t wait to get a closer look, so I started making my way to the palace.

It’s impossible not to notice the eclectic structure that makes up the Pena Palace. The building features a variety of architectural styles, including neo-Moorish, neo-Gothic, and neo-Renaissance. Its bright coloured walls help create the perfect fairytale setting, but it’s also worth admiring its interior which was left pretty much untouched since the last Portuguese royals left in 1910. Inside, you’ll find rooms decorated with tiles, European furniture and oriental porcelain. If you have time, make sure to explore the surrounding park as well, which is full of hidden pathways and small lakes. For the best view of the park, I climbed up to the highest peak called Cruz Alta.

It was a tiring day, but I decided to drive a bit further for a meal at Curral dos Caprinos, a local restaurant known for serving cabrito (young goat meat). I ordered the grilled cabrito, which was very tasty and more than enough to fill me up for dinner.

Map for day 1 of this Sintra tour

Day 2

Sintra Beaches and Wineries

While most people visit Sintra for its monuments, Sintra is also home to great beaches and wineries.
If you’re wondering what to do in Sintra besides the main sights, join us and we’ll show you everything you can’t miss.

Morning

I didn’t get a chance to visit Palácio de Monserrate on my first day in Sintra, so that’s the first place I headed the next morning.

Unlike other palaces in the area, Monserrate wasn’t built for the Portuguese Royals, but for an English merchant. Established in the 18th century, it was home to the novelist William Beckford and later Sir Francis Cook, another Englishman and art collector. Both of them transformed the palace and made it into what it is today. Most of the building is a mix between neo-Gothic and neo-Moorish, with Gothic arches all around it. Even the interior is full of these arches and little hallways with marble columns, which I was not expecting at all.

Inside there’s also a library, a billiard room, a chapel and a few other rooms. Most furniture has been taken out, so the focus is on the ornamented walls and ceilings.

After visiting Monserrate, I drove to Convento dos Capuchos. Once a Franciscan monastery, Capuchos is far from the opulent monuments of Sintra. Here, nature takes over, with dense vegetation crawling over granite boulders and the old monk quarters. Inside these quarters, you’ll find nothing more than a stone bed and cork on the walls. Walking through Capuchos was like exploring a hobbit setting, with narrow passages connecting the tiny houses.

I then headed to Praia da Adraga, a hidden beach on the coast of Sintra. The beach was pretty quiet when I arrived, so I was able to sit down and relax for a bit. There was a small restaurant by the edge of the beach, and that’s where I got my lunch. With the ocean in the background, I couldn’t have picked a better place to enjoy a plate of grilled fish.

Afternoon

In the afternoon, I joined a guided tour of the Adega Regional de Colares. This local winery is set in Colares, between the mountains and the coast of Sintra. The team of Iberian Escapes booked the tour in advance, so all I had to do is meet the guide by the door.

We started by visiting the winemaking facilities, where I learned more about the process of making Colares wine, as well as its history. It turns out, Colares has the only vines in Europe that survived the 19th-century phylloxera plague, thanks to the region’s sandy soil and maritime climate. Colares became a Demarcated Wine Region in 1908, and despite its small-scale, it continues to offer some high-quality wines. After touring the vineyard, I had a chance to taste some of them in the main cellar. Besides the Colares official DOC wine, they also produce other wines under the Lisbon region like Chão Rijo, white wine with a citrus aroma.

Once I finished the tasting, I continued onto Praia das Maçãs, driving alongside the tram tracks until I reached the beach. It was much busier than Adraga, but it was still worth the visit. I spent a few hours there enjoying the sun before I headed to Azenhas do Mar.

The drive to Azenhas do Mar didn’t take more than ten minutes, and the views along the way were incredible, with the road overlooking the ocean. I stopped by the Miradouro das Azenhas do Mar, and from here I could capture the whole town, with its whitewashed houses clinging on a cliff. Just below them, was the Azenhas do Mar restaurant where I was going for dinner. I was still able to enjoy a bit of the sunset before the waiter came in with the menu. With the sea so close, there’s no way I would have missed another seafood meal. This time I ordered the grilled octopus served with roasted potatoes and drizzled with olive oil.

I enjoyed exploring this different side of Sintra, and I can’t wait to explore more of the Portuguese coast when I visit Cascais tomorrow.

Map for day 2 of this Sintra tour

Day 3

A Day in Cascais

Spend a day in Cascais and explore some of the best beaches in Lisbon. Along with the beaches, this little coastal town is famous for its stunning scenic attractions. The cliff formations at Boca do Inferno are worth the capture as well as the views across Cabo da Roca, the most western point in Europe.

It’s easy to drive to Cascais, but you can also get a train directly from Lisbon or a bus from Sintra. From cycling along the sea to learning how to surf, you’ll find many things to do in Cascais.

Start your day in Cascais walking around town or relaxing in one of the local beaches. Praia da Rainha beach is right in the center of Cascais. If you’re coming from Sintra, we suggest driving to Praia da Ursa first, a hidden beach along the coast. Then make your way to Cascais, stopping to visit a few attractions like Santuário da Peninha, and Praia do Guincho. Before heading to the town centre, make sure to stop by Cabo da Roca, and Boca do Inferno, two famous sights near Cascais. You can also visit them in the afternoon and catch the sunset there. It’s up to you. 

Morning

I’ve been staying in Sintra for two days and covered most of the main attractions. Now, I’m heading to Cascais for the day. Instead of going straight to town, I’ve decided to make a few stops along the way.

My first stop was Praia da Ursa, a secluded beach near Sintra. It wasn’t easy climbing down the steep trail to the beach, but it was worth it to see the enormous sea stacks up close. These rock formations come in a variety of shapes, and one of them gave the name to the beach, as it resembles a bear (urso).

The access to the beach can be difficult for some, but if you can make it, it’s definitely worth the visit.

Close to the beach is Cabo da Roca, a rugged headland considered the most westerly point of mainland Europe. Standing 150 metres above sea level, it offers a panoramic view over the Atlantic and the Sintra mountains, as it stands between both. The Portuguese poet Camões described Cabo da Roca as the place “where the land ends, and the sea begins”. These words appear on a memorial stone in Cabo da Roca, along with the coordinates and the label of the westernmost point in Europe.

Go past the main viewpoint, and take some time to walk around the coastline, following the trails to the lighthouse or towards the left of the monument.

After visiting Cabo da Roca, I continued driving to Santuário da Peninha. Set amid the Sintra Mountains this old sanctuary is closed to the public, but its terraces provide great sea views. It can get a bit windy up here, so make sure to bring a coat with you.

Back on the road, I set off to visit Praia do Guincho. Unlike Praia da Ursa with its steep cliffs, Praia do Guincho is made up of a wide sandy stretch surrounded by low dunes. It’s clear the waves are the main attraction here as you spot surfers going in and out of the water. If you’re tempted to join in, you can rent a board or book a surf lesson directly at the beach.

For lunch, the team of Iberian Escapes recommended going to Fortaleza do Guincho. Overlooking the beach, this Michelin-star restaurant specializes in fresh seafood but also serves some delicious desserts.

Afternoon

From Guincho, I drove to Boca do Inferno. Translated as “Hell’s Mouth”, this staggering cliff formation was carved out by the sea, and it’s now one of the most famous sights in Cascais. As I walked along the cliff, I could see the waves splash into the open cave below me. In the summer, it seems quiet, but winter brings rougher waves, and that’s when you’ll see water spraying from the cave.

There’s a bike path from here to Cascais, but I decided to keep driving to the centre, and then spent the rest of the day wandering around on foot.

I visited the Farol de Santa Marta, a small lighthouse museum. Then I went across the street to the Marechal Carmona park. Inside, I found the Museum of Conde de Castro Guimarães. Facing the sea, this former palace features several paintings, ceramics and a library stocked with over 25,000 books. I also enjoyed walking around the park itself and capturing the peacocks and the ducks swimming by the lake.

After the park, I walked to the Cascais Marina. Besides the boat berths, the marina also has a few restaurants where you can stop for a drink. On the way to the centre, I passed through Cidadela, an old fort built between the 15th and the 17th century that is now home to a hotel.

I continued down the road and spent the next couple of hours exploring the streets of Cascais.

For dinner, I went to Hífen, a small restaurant located near Praia dos Pescadores. I ordered the croquettes as a starter and the Galician octopus as a main, which was cooked to perfection.

This is the end of my trip around Lisbon, as I’m off to Sesimbra and Azeitão tomorrow.

Map for day 3 Cascais Tour