Just a stone’s throw away from Lisbon are Estoril and Cascais. Once, these were sleepy fishing villages, now they serve as summer retreats and golf paradises for the rich and famous – even Bond (James Bond) has a history here. Throw that same stone half an hour’s drive further into the nearby hills and you’ll find yourself in between the fairytale castles and palaces of Sintra. Trot Op! bravely followed in the footsteps of Agent 007, starting by pulling out his best one-liner and ordering a dry martini at the bar.
Never say never, but they probably won’t have to drag me to Portugal against my will anytime soon. Varied and still somewhat underestimated destination that is, with a couple of S-tier cities, beautiful natural wonders and the odd almost completely undiscovered region here and there. The Portuguese Riviera – of which Cascais, Estoril and Sintra are part – is not one of these regions. It’s been a very popular tourist draw for many years. This is mainly because the jagged Atlantic coast makes for quite the pleasant place to stay, but also because it’s super close to Lisbon. This makes it easy to extend your city trip with a few extra sunny days at the beach. You can even make it the base of operations for your entire trip. A direct train connection takes you from Cascais all the way to the famous Praça do Comércio in the centre of the Portuguese capital in just forty minutes. And since Lisbon doesn’t have a beach, decisions will have to be made.
“A direct train connection takes you from Cascais all the way to the centre of Lisbon in just forty minutes”
There is more to Cascais than just getting a tan though. The Costa do Estoril – the region’s official name – has a much richer history than you might think at first glance. As early as the 18th century, wealthy people from the capital – including the royal family – began to set up extravagant summer residences here. During WWII, a lot of other prominent guests started dripping in from abroad. Portugal was neutral territory, which caused the hotels to fill with a mixture of exiled royals, government officials and a myriad of other wealthy people. This concentration of VIPs quickly attracted a crowd of a different sort. Spies started working the bars and hotels, passing on every conversation they deemed important to secret services all over the world. These days, you’ll likely won’t be monitored when visiting Cascais, but the region is still a popular destination. It’s also the most expensive place in Portugal to buy a property. Ask Cristiano Ronaldo, who recently drove in with a truckload of money to buy himself a new villa. Can’t blame the man: view’s great.
Cascais, Estoril & Sintra: discover 11 great sights in the Portuguese Riviera
Just a few kilometres away – tucked away in the forested hills overlooking the coastline – lies Sintra. Once here, you’ll seemingly find yourself in a completely different world, yet as far as history goes it’s actually quite similar to Cascais and Estoril. Due to the cooler climate and pristine surroundings, this town too became a favourite retreat for the wealthy – the main catalyst being the construction of the colourful Pena Palace in 1840. This impressive red-yellow castle, was majestically put on top of a hill to serve as the summer residence of King Ferdinand II. The man was apparently quite pleased with his new place and wouldn’t stop talking about it, which in turn convinced a whole bunch of other nobles to come and build a place for themselves. As a result, the centre of town is now full of extravagant mansions, while almost every hill in the area is covered in palace domains. Sintra is one of the most popular tourist spots in Portugal, which means it gets pretty busy here. Luckily, you don’t have to worry about that, because there are plenty of quieter sites to visit and the surrounding woods make for some splendid hikes. Here are my personal highlights for a trip to the region.
1. Cascais: embrace the good life in the town centre
Despite its noble past, Cascais is an authentic and inviting coastal town. Small fishing boats still litter the harbour, you can go sailing or dolphin spotting from the marina near the citadel, there are some nice beaches right in the centre of town and a beautiful oceanside promenade leads you all the way to Estoril. Further away from the sea, you can get lost in a network of cosy pastel-coloured streets. There are numerous bars and restaurants to be found here. Yellow Street (actually several pedestrianised alleys where the pavement was painted yellow) has the highest concentration of them, but you’ll find some anywhere. I had a great dinner in Cantinho do Avillez: part of a local Michelin chef’s portfolio but with very reasonable prices. Mana was good as well: a hip little place near Yellow Street. Looking for some dessert? Head to Santini: a super popular ice cream parlour – you’ll have to wait in line though. My favourite place in Cascais was the tiny rocky beach overlooking the Santa Maria Lighthouse (see picture above: sadly it was in scaffolding). It’s so photogenic it could go right on a postcard, and all day (and night) long people were chilling and listening to music here.
2. Cycle down the beautiful coastline past Boca do Inferno
Many of the most beautiful places in Cascais are outside of town, so I decided to book a guided cycling tour with the company Boost to see them. When you cycle out of town westwards, you’ll do so on a new and very pleasant bike lane with the ocean on one side and a rugged nature reserve on the other. You’ll also ride past the most exclusive villas and restaurants – CR7 isn’t just going to go for a beer with the downtown plebians. The first stop you’ll make is still close to Cascais and called Boca do Inferno. This is an impressive rock formation with a giant hole in it – carved out by the surf throughout the ages. It reminded me of the famous Azure Window in Gozo – before it collapsed in 2017, bankrupting half the island’s tourist operators in the process. Fantastic spot, and there’s a seafood restaurant right next to it. Another nice place to stop for some food and drinks is Casa da Guia: a bright yellow seaside mansion, surrounded by all kinds of food stalls and shops. I cycled all the way to Guincho Beach before turning back: a wide sandy beach known for its strong winds, making it a hotspot for surfers.
3. Feel like James Bond in Estoril
Estoril is just half an hour’s walk from Cascais and feels less touristy and a bit more residential. This is where most of the exiled royals and their entourage sought refuge during WWII. The wonderfully classic Hotel Palàcio Estoril was one of their favourite haunts, so this is where many of the spies hung out as well. They ordered drinks and made “friends” in the luxurious hotel bars, passing on every conversation they deemed interesting. One of these spies was Ian Fleming, who started writing his first James Bond story here: inspired by his own experiences (and apparently also by those of his friend Christopher Lee: Saruman in Lord of the Rings, and working as an RAF saboteur at the time). That first story was called Casino Royale, and the title refers to Casino Estoril next door. This is one of the largest casinos in Europe, and yet strangely not used as a location for the Daniel Craig movie bearing the same name (it was in On her Majesty’s Secret Service though). The Hotel Palàcio Bar still looks great, and is the perfect place to fire some Bond one-liners at random people while you order a martini in the place he was born. Shaken, not stirred, of course. You might as well pour it down the drain if not.
4. Discover the palaces and gardens of Sintra
The hills around Sintra – full of eucalyptus and cork trees – are ideal for a brisk hike (or a jeep tour to see more of the area in one go). The town itself however – filled to the brim with UNESCO World Heritage by the way – can feel a tad less peaceful. It looks fantastic, but the chances are close to zero that it won’t be overrun by tourists before you even get there. The main attractions in Sintra are the palaces in the hills, but the town centre has a lot to offer as well. The main focal point here is Palácio Nacional de Sintra, with its two conical white chimneys. This is one of the oldest palaces in the country, and inside everything is well preserved, showcasing wonderful mosaics and plenty of Moorish influences. Right across from the palace on the same square is cosy Café Paris: a restaurant open since WWII, where you can order numerous Portuguese classics. Sweet tooth? Try out some local pastries at Piriquita Bakery instead and then just wander the streets a bit before heading out to the palaces. Small tip for those of you driving: try and park as low and early as possible and just walk the rest of the way. Almost every street is one way only, which means that if you accidentally drive past something, you’ll have to go through what could be a 45 minute loop to end up back where you started – just saying.
5. Pena Palace & Quinta da Regaleira: Sintra’s most popular palaces
Most visitors to Sintra don’t linger in the city centre for too long, but quickly make their way to one of the following two palaces. Pena Palace is the most famous one, but by far the busiest as well. It’s a fantastically designed, almost unrealistically colourful building, overlooking the surrounding area on top of a hill. The design is eclectic – a mixture of Moorish, neo-Gothic and Romantic influences – and inside you can still see several rooms with their original furniture. There’s a huge and beautiful 200 hectare garden surrounding the palace, full of little pathways, ponds, bridges and half an encyclopaedia worth of tree and plant species. Buy your tickets well in advance.
Slightly less popular but still very busy is Quinta Da Regaleira. This is not a royal palace, but the brainchild of an eccentric Portuguese-Brazilian millionaire with a fascination for the Lodge. As a result, the entire complex is imbued with Freemasonry symbolism. The main building looks completely different from Pena Palace, and is mainly inspired by neo-Gothicism, with countless little spires and gargoyles all over it. This gives it a bit of a Dracula vibe, especially with the fog veiling it. The surrounding gardens were also designed with the Lodge in mind. The most fascinating structure is the so called Initiation Well. It looks like an inverted Tower of Pisa, where you descend 27 metres underground via a spiral staircase. Once there, artificial caves lead you to other parts of the complex. What actually happened here, no one knows for sure. The main theory is that it was intended for the initiation of new lodge members. Also not known is whether or not they had to get really drunk to pass the test, but I sure hope so.
6. Monserrate Palace and the Moorish Castle: less crowded Sintra stops
Want to visit some less busy Sintra sights instead? There are plenty of excellent options available. Monserrate Palace for example, lies a bit further out of town and looks like it was taken straight out of Disney’s Aladdin. This wonderful palace is covered in Moorish and Indian ornaments, which makes for an exotic view. There are immense gardens around the building to explore, home to the ruins of the original chapel built on this site first, and plenty of ponds, little waterfalls and spectacular trees to enjoy. Unlike in the previous two palaces, you’ll often be walking around by yourself here – especially in the gardens.
For a completely different experience, head to the Moorish Castle. This is a much older structure built by – yes – the Moors on top of the hill overlooking Sintra. Unlike the other sites, this is not a palace but a military stronghold. It was partly restored by King Ferdinand in the 19th century (it’s close to his Pena Palace so it suited him well). Today you can combine both sites in one go, but this one will generally be way less crowded. The watchtowers and battlements winding over the hill make the place look like a mini-version of the Great Wall of China. This is of course quite cool, and the views from up here are fantastic.
7. Cabo da Roca: visit the spot where Europe ends
Cabo da Roca is about half an hour’s drive away from Cascais, and offers quite the splendid view as well: a photogenic red and white lighthouse looking out over the ocean from a steep and foreboding cliff. This is the westernmost point of continental Europe, which means that between these cliffs and the Americas, there’s only the Azores and a few thousand miles of open water. Before Columbus landed in the Bahamas, this was actually assumed to be where the world ended – a place where krakens lurked and sirens lured unsuspecting sailors to a watery grave. Today we know better of course, and Cabo da Roca is now a popular tourist stop where people come and take selfies with the ocean as a backdrop. Don’t overdo it though, because more than once the hunt for the perfect holiday picture ended with a tourist pancake to be scraped off the slippery rocks below. The sirens are apparently quite real for some people.
8. Azenhas do Mar: relax in a picturesque coastal village
Just a few minutes from Cabo da Roca lies Azenhas do Mar: perhaps one of the most photogenic villages in Portugal. Just 800 people live here, and the white houses were built directly on the cliff. This created a pleasant maze of little alleys, terraces and courtyards, all with a wonderful view over the water. The whole thing reminded me of Santorini, but with a fraction of the tourists (when I was there, there were barely any). Azenhas do Mar is the perfect place to take a breather or have some lunch. There’s even a mini beach at the bottom of the village. It often floods at high tide, turning the whole thing into a saltwater swimming pool, seperated from the ocean by the walkway around it.
9. Go for a Portugese cooking workshop in Cascais
There’s a pleasant covered market in central Cascais, called Mercado da Vila. Early in the morning, people sell their catch here, together with all the vegetables you’ll need to prepare them, but the venue is open all day. About ten years ago it got completely renovated, which means you’ll now find all kinds of bars and restaurants here (both in- and outside). Marisco na Praça for example, sells fresh fish and seafood you didn’t even know existed. Cascais Foodlab on the other hand – also inside of the Mercado – offers Portuguese cooking workshops led by a local cook and Ukrainian pastry Yuliia. She’s hilarious and bubbly, which makes you stress less about screwing up the food. We prepared a couple of Portugese tapas: breaded cod balls, fried beans and delicious strips of steak with a homemade sauce. Very tasty, and we got to eat all of it right after finishing up. Don’t do this workshop right after lunch like we did. You won’t be able to finish your food, which will make you feel quite bad about yourself.
10. Sports in Cascais: golf and horse riding through the forest
I’ve never played golf myself, so don’t expect a professional opinion on the matter, but Cascais and Estoril are top tier golf destinations. No less than eighteen courses are available, some of which are of international top level. My hotel was full of retired Brits enthusiastically flocking to the bar every night, just to be all in the lobby with their golfbag ready in the early morning. I decided to go horseback riding in the forest, and did so in Escola Rui Barroso. This is a huge riding school in a wonderful patch of nature, where you can book a ride on any level. Since my level was a couple of floors below zero, someone walked next to me so I wouldn’t just fall off my horse like some idiot. Advanced riders can take much more extensive tours – which sounds like a lot of fun.
11. Interesting museums in Cascais
Chances are quite slim, but if you’re faced with a couple of rainy days, there’s a lot of museums in Cascais to keep you occupied. Here’s a small selection:
–Palácio Condes de Castro Guimarães: beautiful early 20th century palace full of antique furniture and splendid halls. It’s located across from the lighthouse and the rocky beach mentioned above – you can even lie down on your towel and get a tan at the foot of the building.
–Museu da Vila de Cascais: compact but fascinating museum on the history of Cascais and how it grew from a fishing village to a fashionable seaside resort.
–Casa das Histórias Paula Rego: museum in a striking red pyramid-like building, dedicated to Portuguese artist Paula Rego.
–Museu do Mar Rei D. Carlos: maritime museum on Cascais’ seafaring past.
–Museu da Música Portuguesa: museum of Portuguese music, full of old instruments and other relics (located in Estoril).
Useful info for a trip to Cascais: hotels and activities
My home away from home in Cascais was Vila Galé Cascais. This is a large hotel near the lighthouse. It comes with a big swimming pool, an outdoor drinking area, a breakfast restaurant and a bar that stays open quite late. The rooms are spacious and the beds are great, but the interior could benefit from a light retouch.
For more information about Cascais, surf to www.visitcascais.com.
For more information about Sintra, surf to www.sintraportugaltourism.com.
Looking for some other European trips? Check out my articles on Porto, Malta and Crete.
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