[Disclaimer: this blog post contains content from a press trip in collaboration with Cacais Tourism Board]

Situated along the stunning Portuguese coastline, Cascais is a charming seaside town that effortlessly combines history, natural beauty, and a vibrant atmosphere. Whether you're a culture enthusiast, a sun-seeker, or an avid adventurer, Cascais has something for everyone. Even remote workers.

In this blog post, we will delve into the must-see attractions, hidden gems, delectable cuisine, and practical tips to make the most out of your Cascais experience as a digital nomad.

An introduction to Cascais

Cascais, with its rich history and enchanting coastal beauty, has long been a beloved destination for travellers seeking a blend of work and leisure. Originally a humble fishing village, Cascais gained prominence in the late 19th century when King Luís I of Portugal chose it as his summer residence. The royal patronage attracted the attention of the Portuguese aristocracy, who built magnificent mansions and transformed Cascais into a fashionable resort town.

Today, Cascais retains its old-world charm while offering modern amenities that make it an ideal place for a workation. Its close proximity to Lisbon, just a short drive or train ride away, provides easy access to the city's business hubs and international airport. Cascais boasts a thriving entrepreneurial community, with numerous coworking spaces that cater to the needs of digital nomads.

The town's natural beauty is a major draw for workation enthusiasts. With its stunning beaches, rugged cliffs, and lush green parks, Cascais offers an inspiring backdrop for work and relaxation. The soothing sound of crashing waves, the invigorating sea breeze, and the panoramic coastal views create an atmosphere that fuels creativity and productivity.

Cascais is also known for its excellent quality of life. The town boasts a vibrant cultural scene, with art galleries, museums, and music festivals that provide ample opportunities for inspiration and entertainment. Its diverse culinary offerings, from traditional Portuguese dishes to international cuisine, ensure a delightful gastronomic experience for digital nomads seeking a culinary adventure.

In addition to its natural and cultural attributes, Cascais is a safe and welcoming destination, making it easy for digital nomads to feel at home. The town's efficient infrastructure, reliable internet connectivity, and supportive business environment contribute to a seamless workation experience.

Whether you're seeking a peaceful coastal retreat, a vibrant cultural experience, or a thriving business community, Cascais offers the perfect blend of work and leisure. Its historical significance, coupled with its natural beauty and modern amenities, make it a truly exceptional destination for digital nomads looking to maximize productivity while enjoying the best of what Portugal has to offer.

A long weekend guide for digital nomads

As a digital nomad, finding the perfect destination to combine work and exploration can be a challenge. Not when you visit Cascais however! Although I actually spent a lot longer in Cascais, this is how I would spend a long weekend in town to make sure I still got the most from my experience while still having time to keep up with my business needs.

Day 1: Getting Settled and Exploring the Town

Morning
Arrive in Cascais and settle into your accommodation. I stayed at LunaHouse, a coliving space just behind Cascais Old Town which had everything that I needed from a comfortable room to the cowork space and pool downstairs. They also provided breakfast in the morning, plus activities each day and a multipurpose room that can be used for yoga lessons and meetings.

Afternoon
Discover the charming old town of Cascais on your lunch break or kick the weekend off early. Meander through the narrow cobblestone streets, explore local boutiques, and indulge in traditional Portuguese delicacies. My suggestions for an afternoon coffee would be a gelato from Santinis or a coffee and ‘brigadeiro’ from A Bijou de Cascais. Use the cowork space at LunaHouse to finish the last tasks of the week before signing off for the weekend.

Evening
Enjoy dinner at one of Cascais' renowned restaurants, like Taberna Clandestina - which I cannot say enough amazing things about. The lovely team at Cascais Tourism booked the experience for me, and it was lucky they did because there were people waiting nearly the entire time I was there. You can discover more about the food and amazing vibe over on my Instagram, but this was absolutely the best place to be on a weekend night!

Day 2: explore the museum quarter and further

Morning
Start the day slowly with breakfast from LunaHouse before heading out to Cascais Old Town for the day. Pick 2-3 places you would definitely like to see, note them down on Google Maps or a town map and set off. Luckily, the main sites are mostly a short walk from each other in the Museum Quarter. I’ll list some of the top recommendations below.

Afternoon
If you’re not too tired, or want to take a break to enjoy the sea breeze, take a walk along the promenade to Praia da Conceição or Praia da Ribeira for a refreshing break. Bask in the sun, take a dip in the azure waters, and unwind. Or head in the opposite direction to Boca do Inferno, a chasm into the seaside cliffs that are a site to behold. But please be careful when you take your photos!

Evening
After a busier day of exploring, I’d recommend returning to LunaHouse to freshen up for dinner before heading back to the old town. On this evening, I tried the slower paced O Pescador restaurant, which if you like fish is a must and then checked out the fashion show that happened to be going down around the corner in the square.

Day 3:surf’s up sunday

Morning
Starting the day a little slower again with breakfast at LunaHouse, being sure to eat good energy food, I then got a transfer to Praia do Guincho for a surf class with Wanted Surf School. It is possible to cycle to the beach in about 40 minutes, but a transfer was worth it just for how tired I was feeling afterwards.

Afternoon

After a two hour class of admiring the scenery and using a lot of physical energy to hold your balance and catch waves, you’re going to want to have snacks ready back at your accommodation. Maybe taking a dip in the pool back at LunaHouse or taking a nap to feel refreshed again for dinner.

Evening
Take the walk slow back to the beach front to people watch for a bit before dinner at Cappriciosa. There’s normally music playing from at least one group on the beach and the view over the water is beautiful. Head to the restaurant, making sure you get a seat looking over the beach and harbour for sunset.

Surf class with Wanted Surf School at Praia do Guincho

Day 4: exploring Sintra and the region

Morning

You can’t leave Cascais (or Lisbon) without taking at least one day to explore Sintra - although I heavily recommend making time for two days, with a stay overnight in town.

Consider taking a tour company such as Tuga Trips as they will be able to provide you with an entertaining day and great insights. We started the morning driving thirty-ish minutes to Montserrate Palace. Nestled amidst lush gardens, this architectural gem boasts a unique blend of Gothic, Moorish, and Indian influences and is surprisingly less visited than other sites in town.

After wandering around, grab an espresso and queijada, a popular sweet treat from Sintra.

Afternoon
Head into Sintra's charming old town, a UNESCO World Heritage Site for lunch. Here, you'll discover narrow cobblestone streets, colourful buildings, and delightful cafes. We grabbed lunch at Cafe de Paris right in the centre of the buzz, which I would do again just for their amazing juices! João, my guide, recommended I then take a little walk around, trying a ginjinha shot from a chocolate cup at Bar do Binho (which I also recommend you do the same). It’s essentially a berry liquor shot in a shot cup made of entirely chocolate.

On your way out of the old town, both João and an Uber driver from a previous day trip I did to Sintra, recommended stopping at Casa do Preto for a coffee and travisseiro: another sweet treat from Sintra. And I will pass this local secret on to you as well because it was super worth it!

Finish off your day trip with a beautiful drive through the countryside back to venture to Cabo da Roca, the westernmost point of continental Europe. Although it’s super windy, it’s worth it for the views - although please don’t go passed the warning signs… the photos aren’t worth potentially being blown off the cliffs.

If you then have the energy to head out for dinner then kudos! Me, I just grabbed a snack from the Auchan supermarket and put my feet up for the rest of the evening. (Uber Eats and Glovo are also convenient options).

If you have time for another day in Sintra…

I would actually do this day first and then the tour I described above the second day on the way back to either Cascais, Lisbon or the airport.

Ahead of time, I would book a slot to visit Pena Palace, making sure to also either book an Uber or get the bus up the hill. Especially in the warmer months. Although this palace is normally flooded with crowds from 9am, it is worth a visit to this palace just to see the beautiful tiles and park. I visited the gardens for an hour first - which was worth it just to have them pretty much to myself and the gardeners - and then head into the palace.

The walk down to the town isn’t as bad, so if you’re feeling brave, give it a go so you can wander through some of the quieter back streets and see the beautiful houses. I had a quick lunch at the palace, but there are a lot of restaurants on route with ‘the best views of Sintra’ to stop at.

I then used the rest of my time to explore Quinta da Regaleira, which I preferred visiting to Pena Palace in all honesty. Another UNESCO World Heritage Site, it’s like one big lush adult playground with a Manor House, a well, caves, gardens and a lake. All with an intention and story.

Top recommended sites to see in Cascais

There are of course a few to check out, and some are also free to enter like the House of Advertising, but the following were the top recommended places to visit in town:

The Cascais Town Museum: (free entry) located in the heart of the town, it delves into the rich history and cultural heritage of Cascais. The museum offers a comprehensive journey through time, showcasing the evolution of Cascais from a humble fishing village to a vibrant seaside resort. Inside, visitors can explore a wide array of exhibits, including archaeological artifacts, traditional costumes, historical photographs, and interactive displays. The museum provides a captivating insight into the town's maritime traditions, royal connections, and artistic influences.
Paula Rego Museum: dedicated to the renowned Portuguese artist Paula Rego, this museum celebrates her unique and thought-provoking works. Located in the charming Casa das Histórias, designed by the famous architect Eduardo Souto de Moura, the museum showcases a comprehensive collection of Rego's paintings, drawings, and prints. The museum's architecture, combined with the artist's powerful storytelling, creates an immersive and captivating experience.
Casa de Santa Maria: this museum offers a glimpse into the elegant lifestyle of the 20th-century aristocracy. Set in a beautifully preserved mansion, Casa de Santa Maria showcases the interior decor, furniture, and artwork of the former owners. Visitors can admire the lavish rooms, stunning gardens, and enjoy panoramic views of the Cascais coastline. The museum also hosts temporary exhibitions. (It’s also worth taking the short walk over to the lighthouse and museum (which is free to enter).

Cascais offers an ideal setting for digital nomads seeking both productivity and adventure. By following this itinerary, you can hopefully make the most of your time in Cascais, striking a balance between work and exploration, and enhance your online presence through SEO-friendly content. Embrace the coastal beauty, delve into the local culture, and make the most of your long weekend in this remarkable destination.

So the question really is: is Cascais on your workation list yet?

Han x

Ps. if you decide to book an apartment instead of a coliving space, I’ve put together a short video of some the cafes I remote worked from here.

How to spend a long weekend in Cascais as a digital nomad