Just a stone’s throw away from Lisbon lie Cascais and Estoril. Once sleepy fishing villages, they later grew into elegant summer retreats and golf paradises for the rich and famous – even James Bond has a history here. Throw that same stone about half an hour inland, into the forested hills overlooking the coast, and you’ll suddenly find yourself among the fairytale palaces and castles of Sintra.
Cascais, Estoril and Sintra sit right next to each other on Portugal’s Atlantic coast and are often visited on the same trip. Together, they form the heart of the Portuguese Riviera: a region that combines beaches, historic seaside towns and cooler, forested hills full of extravagant palaces. Cascais in particular makes an excellent base, thanks to its lively centre, beaches right in town and a direct train connection to Lisbon.
Why visit Cascais, Estoril & Sintra?
Never say never, but they probably won’t have to drag me to Portugal against my will anytime soon. It’s a varied and still somewhat underestimated destination, with a couple of S-tier cities, beautiful natural wonders and the occasional almost completely undiscovered region. The Portuguese Riviera – of which Cascais, Estoril and Sintra are part – is not one of those hidden gems. It has been a popular travel destination for many years, and for good reason.
The jagged Atlantic coastline makes this part of Portugal a wonderfully pleasant place to stay, especially in summer. Just as important is its proximity to Lisbon. Cascais is connected to the Portuguese capital by a direct train line that takes you all the way to Praça do Comércio in about forty minutes. Since Lisbon itself doesn’t have a beach, decisions will have to be made – and many travellers choose to base themselves by the sea instead.
“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. As early as the 18th century, wealthy Lisbon families – including the royal court – began building extravagant summer residences here. During WWII, Portugal’s neutral status attracted a very different crowd: exiled royals, diplomats and government officials from all over Europe. Where VIPs gather, spies tend to follow, and soon the bars and hotels of Estoril and Cascais were buzzing with intelligence agents quietly passing on information to their respective secret services.
One of them was Ian Fleming. While spending time in Estoril, he drew inspiration from the casino next door, the hotel bars and the people he met there – experiences that would later find their way into his first James Bond novel, Casino Royale. These days, you’re unlikely to be monitored while ordering a drink, but the region has lost none of its appeal. In fact, Cascais is now the most expensive place in Portugal to buy property. Ask Cristiano Ronaldo, who recently arrived with a truckload of money to buy himself a new villa. Hard to blame the man – excellent views.
Just a few kilometres inland lies Sintra, tucked away in the cooler, greener hills of the Serra de Sintra. While it feels like a completely different world, its history mirrors that of Cascais and Estoril. Thanks to its mild climate and pristine surroundings, Sintra became a favourite summer retreat for the Portuguese elite as well. The main catalyst was the construction of the colourful Pena Palace in 1840, built high on a hill as the summer residence of King Ferdinand II. Apparently quite pleased with his new home, the man wouldn’t stop talking about it, which in turn convinced many other nobles to follow suit. he convinced many other nobles to follow suit.
“Half an hour inland, Sintra feels like a completely different world – cooler, greener and filled with extravagant palaces.”
The result is a town surrounded by extravagant palace domains and forests full of walking trails. Sintra is now one of the most popular tourist destinations in Portugal, which means it can get busy – very busy. Luckily, beyond the headline attractions, there are plenty of quieter palaces, gardens and hiking routes to explore, especially if you plan your visit well.
Cascais ties all of this together. From here, you can walk to Estoril, take easy day trips to Sintra, explore dramatic coastal viewpoints like Cabo da Roca, or simply stay put and enjoy the beach. Below are my personal highlights for a trip to Cascais, Estoril and Sintra – from historic town centres and palaces to coastal day trips, food experiences and a few lesser-known stops in between.
Cascais: beaches, food & laid-back coastal life
Cascais manages to balance an upscale look with a genuinely relaxed atmosphere. There are beaches right in town, plenty of good restaurants, a very scenic coastline to explore and just enough history to remind you the place has been popular for quite a while – long before international tourists started rolling in.
Cascais town centre: embrace the good life
Despite its noble past, Cascais is an authentic and inviting coastal town. Small fishing boats still litter the harbour, while the marina near the citadel is the starting point for sailing trips and dolphin-watching tours (here’s a good dolphin tour in a small speed boat). There are several nice beaches right in the centre of town, and a beautiful oceanside promenade leads all the way to Estoril.
Further away from the sea, you can get lost in a network of cosy, pastel-coloured streets. Bars and restaurants are everywhere. Yellow Street – actually a cluster of pedestrianised alleys where the pavement has been painted yellow – has the highest concentration, but you’ll find good places dotted all over town. I had a great dinner at Cantinho do Avillez: part of a local Michelin-starred chef’s portfolio but with very reasonable prices. Mana was excellent as well: a hip little spot close to Yellow Street.
For dessert, head to Santini: a hugely popular ice cream parlour where you’ll almost certainly have to queue. My favourite place in Cascais, though, was the tiny rocky beach overlooking the Santa Maria Lighthouse. It’s so photogenic it could go straight on a postcard, and day and night you’ll find people lounging here, listening to music and watching the sun dip into the ocean.
Tip: you can go sea kayaking with a guide in Cascais, which is lots of fun. Click here for booking.
Cycling the coast: Boca do Inferno & Guincho
Many of Cascais’ most beautiful spots lie just outside town, so I booked a guided cycling tour with Boost to explore the coastline. Cycling westwards, you’ll follow a new and very pleasant bike lane, with the ocean on one side and a rugged nature reserve on the other. Along the way, you’ll pass some of the most exclusive villas and restaurants in the region – Cristiano Ronaldo is unlikely to join you for a beer in the downtown pub.
The first stop is Boca do Inferno: an impressive rock formation carved out by the surf over centuries. A giant hole in the cliffs allows the waves to thunder through, creating a dramatic spectacle. It reminded me of Gozo’s famous Azure Window – before it collapsed in 2017, bankrupting half the island’s tourism industry in the process. There’s also a seafood restaurant right next to it, making this a perfect lunch break.
Another great lunch stop is Casa da Guia: a bright yellow seaside mansion surrounded by food stalls, cafés and small shops. I cycled all the way to Guincho Beach before turning back: a wide, sandy stretch known for strong winds and big waves, making it a hotspot for surfers and kitesurfers.
Portuguese cooking workshops & local markets
Right in the centre of Cascais you’ll find Mercado da Vila: a pleasant covered market that was completely renovated about ten years ago. Early in the morning, locals sell fresh fish and seafood alongside fruit and vegetables, but the market stays lively throughout the day thanks to its bars and restaurants.
Marisco na Praça for example, sells fresh fish and seafood you probably didn’t even know existed. Cascais Foodlab – also located inside the market – offers Portuguese cooking workshops led by a local cook and Ukrainian pastry chef Yuliia. She’s hilarious and bubbly, which helps you stress a little less about messing things up.
During the workshop, we prepared several Portuguese tapas, including breaded cod balls, fried beans and strips of steak with a homemade sauce. Everything was delicious, and we got to eat it all straight afterwards. One piece of advice: don’t book this right after lunch like we did. You won’t be able to finish your food, which will leave you feeling oddly disappointed in yourself.
Sports in Cascais: golf & horse riding
Cascais and Estoril are top-tier golf destinations. No fewer than seven courses are located in the area, some of them of international championship level. I don’t play golf myself, so don’t expect a professional opinion, but my hotel was full of retired Brits enthusiastically gathering in the lobby every morning, golf bags in hand. They were also flocking even more enthusiastically to the bar every night, so I guess they had fun.
I opted for a different kind of activity and went horse riding in the nearby forest at Escola Rui Barroso. This large riding school is set in a beautiful natural area and caters to all levels. Since my own level was several floors below zero, someone walked next to me to make sure I didn’t fall off like an idiot. More experienced riders can book longer rides through the surrounding countryside, which sounds like a lot of fun.
Museums in Cascais
If you happen to catch a few rainy days – slim chance, but still – Cascais has plenty of museums to keep you entertained. Here are a few highlights:
–Palácio Condes de Castro Guimarães: beautiful early-20th-century palace filled with antique furniture and impressive halls. It sits right next to the lighthouse and rocky beach mentioned earlier – you can literally sunbathe at the foot of the building.
–Museu da Vila de Cascais: compact but fascinating museum detailing the town’s transformation from fishing village to seaside resort.
–Casa das Histórias Paula Rego: museum in a striking red, pyramid-like building, dedicated to the work of Portuguese artist Paula Rego.
–Museu do Mar Rei D. Carlos: maritime museum focused on Cascais’ seafaring past.
–Museu da Música Portuguesa: small but interesting museum (in Estoril), full of historic Portuguese instruments and musical heritage.
Estoril: James Bond, spies & grand hotels
Just half an hour on foot from Cascais, Estoril feels slightly less touristy and a bit more residential. It’s calmer, more stately, and still looks and feels like a place that once hosted Europe’s elite – as well as some more secretive visitors.
Hotel Palácio, Casino Estoril & Bond history
During WWII, many exiled royals and their entourages sought refuge in Estoril. One of their favourite haunts was the wonderfully classic Hotel Palàcio Estoril. As spies tend to follow the diplomats and aristocrats, the hotel soon became a magnet for them as well.
Agents from various intelligence services worked the hotel bars. They ordering drinks, struck up conversations, made “friends” and quietly passed on anything they deemed important. One of them was Ian Fleming, who spent time in Estoril during the war and later began writing his first James Bond story here. His inspiration came not only from his own experiences, but also from those of his friend Christopher Lee – later famous as Saruman in The Lord of the Rings, but at the time working as an RAF saboteur.
That first story was Casino Royale, named after the Casino Estoril next door. Today, it’s still one of the largest casinos in Europe, although it was never used as a filming location for the Daniel Craig film of the same name (it was in On her Majesty’s Secret Service though). The Hotel Palácio bar still looks fantastic and is the perfect place to order a martini while casually dropping a few Bond one-liners at unsuspecting strangers. Shaken, not stirred, of course. You might as well pour it down the drain if not.
Sintra: palaces, gardens & forested hills
Just a short drive inland from Cascais, Sintra feels like another world. Cooler, greener and more dramatic, its hills are packed with extravagant palaces, dense forests and wonderful walking trails. It’s one of Portugal’s most visited destinations – but with a bit of planning, it’s still possible to experience its quieter, more atmospheric side.
Exploring Sintra town
The hills around Sintra, filled with eucalyptus and cork trees, are ideal for a brisk hike – or for a jeep tour if you want to see more of the area in one go. The town itself, however, can feel a little less peaceful. Sintra is filled to the brim with UNESCO World Heritage, and while it looks fantastic, the chances are close to zero that it won’t be busy by the time you arrive.
That said, the town centre is well worth exploring. Its main focal point is the Palácio Nacional de Sintra, instantly recognisable by its two conical white chimneys. This is one of the oldest palaces in Portugal, and the interior is beautifully preserved, with intricate mosaics and clear Moorish influences.
Right across the square from the palace is Café Paris: a cosy restaurant that has been open since WWII, serving a solid selection of Portuguese classics. Sweet tooth? Head to Piriquita Bakery instead to sample some local pastries, then simply wander the narrow streets for a while before heading up into the hills.
Small tip for those driving: try to park as low and as early as possible and walk the rest of the way. Almost every street is one-way only, which means that if you accidentally drive past something, you’ll find yourself stuck in a 45-minute loop just to end up back where you started.
Pena Palace & Quinta da Regaleira
Most visitors don’t linger long in Sintra town, but quickly make their way to one of the surrounding palaces. Pena Palace is the most famous – and by far the busiest. Perched on top of a hill, this wildly colourful building looks almost unreal, with its eclectic mix of Moorish, neo-Gothic and Romantic influences. Inside, several rooms still contain their original furniture, offering a glimpse into royal life. Surrounding the palace is a vast 200-hectare park, criss-crossed with pathways, ponds, bridges and half an encyclopaedia worth of trees and plant species. It’s genuinely beautiful, but you’ll want to book your tickets well in advance if you plan to visit.
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 steeped in Freemasonry symbolism.
The main building is inspired by neo-Gothicism and covered in spires and gargoyles, giving it a slightly Dracula-esque vibe – especially when the fog rolls in. The gardens were also designed with symbolism in mind. The most intriguing feature is the so-called Initiation Well: a 27-metre-deep spiral staircase descending underground, looking like an inverted Tower of Pisa. From the bottom, artificial caves lead to other parts of the estate. What exactly 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.
Monserrate Palace & the Moorish Castle
If you’d rather avoid the busiest spots, Sintra offers plenty of excellent alternatives. Monserrate Palace for example, lies a bit further from the town centre and looks as if it was lifted straight out of Aladdin. Covered in Moorish and Indian ornamentation, it’s one of the most exotic-looking buildings in the region.
The surrounding gardens are vast and surprisingly quiet, home to the ruins of an earlier chapel, winding paths, ponds, small waterfalls and an impressive collection of trees from around the world. Unlike at Pena Palace or Quinta da Regaleira, you’ll often find yourself wandering around on your own here – especially in the gardens.
For a completely different experience, head to the Moorish Castle. Built by the Moors on top of a ridge overlooking Sintra, this isn’t a palace but a military stronghold. It was partly restored by King Ferdinand II in the 19th century – conveniently close to his beloved Pena Palace.
Today, the castle’s battlements and watchtowers still snake across the hills like a miniature Great Wall of China. It’s generally far less crowded than the palaces below, and the views from up here are spectacular.
Day trips from Cascais & Sintra
One of the biggest advantages of staying in Cascais is how easy it is to explore the surrounding coastline and countryside. Within half an hour, you can stand on Europe’s westernmost tip, wander through a near-empty coastal village or combine dramatic scenery with a lunch by the sea.
Cabo da Roca: visit the spot where Europe ends
Cabo da Roca lies about half an hour’s drive from Cascais and offers one of the most dramatic viewpoints in the region. photogenic red-and-white lighthouse looking out over the Atlantic 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 widely believed to be the place where the world ended. A realm of krakens, sirens and other unpleasant creatures waiting to lure sailors to a watery grave. These days we know better, of course, and Cabo da Roca has become a popular tourist stop where visitors come to take selfies with the ocean as a backdrop. 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.
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. Only about 800 people live here, and its white houses were built directly on the cliff, creating a maze of narrow alleys, terraces and courtyards – almost all with a fantastic view.
The whole place reminded me a bit of Santorini, but with a fraction of the tourists. When I visited, there were barely any at all. Azenhas do Mar is the perfect place to take a breather or have some lunch. There’s even a small 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.
Tip: this great tour leaves from Cascais and takes you to both Cabo da Roca and Azenhas do Mar, as well as to several wineries (with lunch and a tasting) only to end back in Cascais at Casa da Guia.
Where to stay in Cascais?
** There are some (useful) affiliate links in this article. These were personally selected to make sure they actually add value. If you were already thinking of booking a hotel or tour in Cascais, please consider doing so through one of my links. Doesn’t cost you an extra dime and I get a small compensation for my work. Thank you in advance! **
Cascais is an excellent base of operations for exploring the Portuguese Riviera. It’s close enough to Lisbon for easy day trips, but far more relaxed, with beaches, restaurants and coastal walks right on your doorstep. Most visitors will want to stay near the town centre or along the seafront, within walking distance of the beach, the train station and Cascais’ main sights. Here are some good suggestions.
–Vila Galé Cascais: this large hotel near the lighthouse was my home away from home in Cascais. It comes with a big swimming pool, an outdoor bar, a breakfast restaurant and a indoor bar that stays open quite late. The rooms are spacious and the beds are great, but the interior could benefit from a light retouch.
–Grande Real Villa Italia: I stayed here long ago when I was still writing for B2B magazines. It’s almost right next to Vila Galé on the same fantastic location, but this one is a full five star hotel. This makes it more luxurious but also a bit more expensive.
–Hotel Baia: large hotel right on the promenade in the heart of downtown Cascais, overlooking the beach. This is an ideal option if you want to be close to the train station, bars, restaurants and the liveliest part of town.
–Villa Vasco Da Gama: boutique hotel in a lovely building in central Cascais, a bit further away from the coastline but still within an easy walking distance. Surprisingly cheap compared to a lot of other places.
–Hotel Fortaleza do Guincho: spectacular hotel on a cliff looking out on Guincho Beach. It’s obviously further from the city but perfect for people who don’t necessarily want to stay in town.
–Pergola Boutique Hotel: charming option just behind the main promenade. Set in a historic building with a leafy garden, it feels intimate and personal while still being right in the centre of town.
–Farol Hotel: upscale hotel on a dramatic clifftop near the Santa Maria Lighthouse. The views over the Atlantic are spectacular.
–Hotel Cascais Miragem: large, elegant hotel located between Cascais and Estoril. Comes with spacious rooms, sea views and a more resort-like atmosphere, while still being within walking distance of both town centres and the coastal promenade.
Practical tips for visiting the Portuguese Riviera
A little planning goes a long way when visiting Cascais, Estoril and Sintra. These practical tips will help you make the most of your time in the region.
-Best base: Cascais is the most convenient place to stay. It comes with easy train access to Lisbon, beaches within walking distances and a relaxed but still lively atmosphere in the evenings – something Sintra lacks once the day-trippers arrive. Estoril is very pretty but offers less entertainment at night.
-Car vs train: You don’t need a car for Cascais, Estoril or Lisbon; the coastal train line is fast, cheap and reliable. For Sintra and nearby coastal villages like Azenhas do Mar, a car offers more flexibility, but guided tours are perfectly workable alternatives (although most of the Sintra tours seem to leave from Lisbon). GetYourGuide is full of them, so take your pick.
-Best time to visit Sintra: Go as early as possible or later in the afternoon. Midday is by far the busiest period, especially at Pena Palace. Booking tickets in advance is essential during high season.
-How many days do you need: Plan at least 4–5 days to explore Cascais, Estoril and Sintra at a relaxed pace. This allows time for beaches, palaces and at least one coastal day trip without rushing.
-Crowd avoidance tips: Visit popular sights early (only necessary in Sintra), limit yourself to one major attraction per day, and balance busy palaces with quieter places like Monserrate, the Moorish Castle or the forest trails around Sintra.
Further reading
For more information about Cascais, visit the official site: www.visitcascais.com.
For more information about Sintra, visit www.sintraportugaltourism.com.
Looking for some other Southern European trips? Check out my articles on Porto, Malta and Crete.
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