August 3, 2022

I gave up my lease in San Francisco in July and headed to Portugal with my girlfriend. Our original plan was to find a short lease in Lisbon but I got glowing reviews about Cascais, a beach town half an hour west of the city center. Some friends spent a weekend there and raved about the food, the views, and the people. It seemed like a good formula for a remote working stop.

Like most Portuguese cities that I visited, most of the city's architecture is on the older side. There are winding cobblestone streets with intricate detailing of black strands snaking along white tiles. But unlike other towns Cascais is also seeing a wave of new construction fueled in part by the investment incentives that were added after the 08 financial crisis. There were a sea of cranes around the city center with more sprawling their way to Lisbon along the horizon. The hum of the city's activity and the din of construction, coupled with the turquoise water and great food scene, makes it feel like this sleep hamlet is going to fast become an epicenter of european vacations.

But first, my two cents.


Our studio was nice but was way too small for daily work. Before settling on Cascais I researched a few coworking spaces in the neighborhood. There's one closer to town (LACS) and one that's a bit further up in the hills towards Sintra. I tried LACS first for the convenience and was blown away. There were hundreds of entrepreneurs in different stages of company creation, some freelancers, some with full offices. It felt like the WeWorks I've visited but with a more open floor plan so you see all the startups working in a close space. The diversity was particularly notable: decor companies, accounting companies, and software startups. The building is only a few years old and allows 24hour access if you sign up for a month "fix" pass, which gives you a dedicated desk in one of the rooms. The coworking rate mirrored the cheaper property values when compared to Lisbon. A fixed package was $180 a month. It was an easy choice.

I didn't know how big I would find the language barrier, given Cascais is a small town and this is an office park mostly for locals. But mostly everyone was bilingual in English or Spanish, so it was easy to acclimate and meet new people. We quickly got to know our main officemate, who worked Portuguese hours but seemingly didn't sleep. We were working PST and thus the nightshift - around 3pm to midnight on most nights. We called it once at 1am and he was still there working away on a marketing presentation. His work ethic was impressive, his rejection of the sandman maybe even more so. He was also somewhat of a foodie so he gave us a list of his favorite restaurants ranked by price and vibe, most of which made it to my top rankings.

We typically showed up right before the joint cafe closed, so we'd start our afternoon with a cup of espresso. Sometimes a double. I made extensive use of the outside patio with tables and hammocks, especially during phone calls. The weather was nice and there was usually a calm breeze that was a nice break from the office air circulation. For variety I would occasionally switch up my desk. Since I only had my laptop and wasn't tied to a monitor, I'd move to the second floor and then back to the first. It gave me some nostalgia for library hopping back in college. There was a small kitchenette on that second floor where we prepped salads and heated up our meal-prepped food. We'd break for a quick dinner break at 8pm while it was noon in California. Overall, I'm sold on coworking. The spaces are great and lets you minimize the floor print of your housing while assigning work to a physical space. The only thing that would be better is if LACS sold day or week passes that allowed 24 hour access. We only were in Cascais for two weeks so it would have been more economical but I can understand their reasoning.

Working the night shift takes some getting used-to. The biggest thing was compartmentalizing work to the hours that you give it. When you jump into work right after you wake up, you naturally start your day thinking about what you need to do and then get right to it. When you work in the evenings, it's easy to let yourself think about work all day and distract from enjoying the time ahead of you. I still much prefer working in the mornings, so some days I would get up a bit earlier and focus on some deep work before taking a break for the mid-day adventure. It helped with this compartmentalization because I knew I could accomplish some goals right after I got up and then save the rest for the evenings when I can get back into it.

Getting Around

On the left, our route to Sintra. We scootered on the shoulder of a freeway, a bridge, and a long backroad. On the right, the coastal journey. Vinyards, small towns, and an unbelievable view along the cliffs. Go on the right one for at least one leg.

Transit in Cascais is all over the map. Busses decide when to show up. You're not totally sure if the previous one was running late or the next one is early. They have convenient coverage - it was a relatively straight shot from our apartment to the gym and office - but their sporadicalness meant that most days we ended up walking. Most of the actual housing in Cascais is up in the hills around the city center as well, meaning you're in for a half hour hilly walk to get to most of the restaurants and beaches. Good for the occasional stroll but a bit far for daily urban exploring around town.

Rent a scooter. They're very workable for two people and give you far easier access to Cascais. Also they're incredibly fun. I felt right out of Charade when I was zipping down side streets with the sea wind blowing gently around me. After I got the scooter, gym trips became a daily routine and I was able to dash out to the grocery store at a minute's notice to pick up fresh produce. I still made a point to walk around downtown every morning to get my 10000 steps in, but the scooter was a nice shortcut to the city center. Gas only cost a total of 8€ during the course of a two week stay, so it's also a much cheaper way to get around.

The scooters are only 50cc so they needed a regular drivers license, not a motorcycle license. This also means they're not overly powerful and top out at around 50km/h. On hills they struggle a bit and you'll only get up to 35km/h. Luckily most of the roads around Cascais are either slow or have two lanes to allow for easy passing. We were easily able to head to a few remote beaches and towns outside of Cascais, which made our time there far more fun.


Sintra's known as a castle town. There's a small downtown area next to a road that snakes into the hills, with castles and gothic architecture dotting the scenery. Castelo dos Mouros is the most popular since it overlooks the town and countryside; it's also over-hyped, according to most of the locals that we talked to. We headed instead to Quinta da Regaleira. It looks like something out of the middle ages. White stone, spires, and winding gardens that have a variety of plant life. If you actually check on the building date, however, construction only got started in 1900. It was hard to imagine workmen installing battle armaments in the last century. To defend against what exactly? The Model-T I guess.

The castle grounds were the highlight of the place. They have a well called the Initiation Well, which spirals down into the ground and opens up into a branching cave network. It was a popular spot when we were there but the queue moves quickly and you have a decent amount of room once you're side. There's a waterfall to one side and lights that wind the way through the path.

The actual castle was fine. It was limited to the first floor with only a few rooms to walk around in. We got in, learned a bit more about the construction history, and got out. The castle definitely was more there for the aesthetic than function. Outside someone was playing covers of bob dylan songs with half Portuguese, half English lyrics. Helped explain why I failed at singing half the words.

We left our moped by the castle and headed into the heart of town. The main boulevard is swimming with restaurants and gift shops, most of which were selling postcards or azulejos - the quintessential blue and white tile of Portugal. We certainly saw our fair share of these tiles on buildings in Cascais, so they're certainly authentic, but we were in the market for something a bit different. We stumbled upon Olaria de sao pedro because of the store design. The place shimmers with all the hues from the pottery around its perimeter. The woman who was clerking described that they hand-engrave most of their pieces from patterns that stretch back centuries, but with modern paints and a slightly unusual color schemes. We found some tile coasters that caught our eye and bubble wrapped them for the trip back home.

For lunch we went to Tascantiga, a restaurant nestled into one of the side streets. They didn't take a waitlist so there was a gaggle of groups milling around the patio and spilling onto the sidewalk. Once we got seated, their cider was crisp and their fish was particularly standout. The shade of the patio provided a nice relief to the climbing temperatures. They had a funky playlist going on - it felt like a collection of all the 6min+ songs of recent memory. Hotel California, Don't Stop 'Til You Get Enough, etc. Someone on staff had a niche taste in music selection where length was more fundamental than genre.

Once we wrapped up lunch, we wanted to head back to Cascais for sunset. The ring road that runs around the Sintra castles is a one-way for most of its length. We took a wrong turn and ended up tracking this road into the hills, overlooking vineyards and winding into some smaller towns (see map above). The drive was fantastic and eventually we decided to take this way all the way back. We couldn't have been luckier for it. It took us directly along the coastal path, where you're riding with the wind whipping and the Atlantic coast stretching out before you. We also had the road mostly to ourselves so we had a leisurely drive back to Cascais and the beaches along the coast.


It has hills, a red bridge, hipster coffee shops, and trolly cars. The postcards we found could have been out of a San Francisco gift shop.

We took the train in from Cascais, which was a short hour from downtown. It drops you right by the Time Out Market, a ferry terminal like building that bundles a lot of independent restaurants that had original storefronts in the rest of Lisbon. People were packed around the popular places so we shrugged off the idea of lunch and spent our time walking around to see the diversity of food choices. We got a coffee at one of the cafes and strolled through the pleasant stationary store inside the main hall. If you want food try to come at an offpeak hour.

We walked all around Lisbon with the intended destination of the botanical gardens. Lisbon is a solid +10C from Cascais so we made a few pitstops along the way for iced coffee and gelato. On the conversational agenda for the day: how the US is so poor at building subway infrastructure. Not the most local talking point but it's been on my mind recently. From the botanical gardens we switched back down the hills. We found ourselves at a few piazzas with breathtaking views of the water and the buildings on the other side of Lisbon.

For dinner, we went to Mankooche, a Lebanese restaurant that was bundled as part of a large outdoor dining pavilion. There were soft lights running along the tables and the night still had a lingering warmth. They were full on tables when we got there and initially turned us down - until a mother/daughter duo noticed our situation and mentioned they were about to leave. We got lucky. The falafel was fantastic and the chicken kebab was equally as great.

Afterward we tried for a rooftop bar next door at Java. The views were good but it was absolutely jammed with American 18 year olds. We took a lap and huffed it out of there within three minutes. Next time: try going out on the Pink Street or really just anywhere else.


Most of our time downtown was spent exploring restaurants and local shops. We didn't find any standout shops - except for the Farmácia. Our rental didn't come with soap and we found the Farmácia right on Largo Cidade de Vitória 7 to be a mecca for everything personal care. It's certainly the most aesthetic place I've ever purchased shampoo.

Groceries are surprisingly hard to locate. Auchan seems to be where everyone goes for their local purchases, but you'd never know from the facade. It's technically a general store but it has an extensive range of food that beat that local full grocery stores. We didn't realize this until far too late in our travels but we'll know for next time.

The main beach downtown is packed and the water's pretty cold, so it's good for a dip on the hot days but you'll probably not spend a ton of time floating around. Instead Praia do Guincho is the beach to go to. There's also way more room to spread out on the beach compared to ones in Cascais. It's also evidently an incredibly popular kite surfing beach. When we went there after Sintra, we found tens of kites aloft and dotting the sky with a sea of colors: greens, oranges, blacks, purples. There was a range of surfers, kids in their teens all the way up to mid-50s. We regularly saw the pros get 30 feet of air when they dismounted some of the big waves.


Cascais has its fair share of tourist trap restaurants. On some of the streets you'd see ten English menus before you saw a Portuguese one. But there are a host of great restaurants sprinkled around town that blew us away.

Hifen: Popular with the local Cascais crowd, and they know what they're talking about. You simply really can't go wrong with the food here. The chicken sandwich has pesto aioli, sautéed onions, and Dijon. The calamari is perfectly crispy, minimal breading, and the lemon was fresh. Both might be the best that I've had in recent memory. The bartenders mix a host of creative cocktails - picasso acolytes working in shaved ice and spritzers instead of acrylic and canvas. Some modern funk plays in the background. We got a chance to meet some locals and expats, including a couple that recently moved from Texas after their kids graduated high school and moved out. After never being out of the states five years ago, they're clocking 52 countries and settled into Cascais as their european home.

House of Wonders: Walk in the door and they whisk you to the visual menu. Someone walks through the different options - all vegetarian, from bean burritos to sushi rolls to a crisp gazpacho with pomegranates. The lemonade were particularly standout, some mixture of tonic water, limes, and a magic flair. One standard price for any plate for lunch. Even as carnivores, this place kept us coming back for more.

Palaphita: A true room of requirement. We had an hour to kill before we were seated across the way at Dom Grelhas. We hear berlin underground music coming from a nearby campground and take a stroll down that way just to see what was going on. This place looks like something out of Burning Man. They have three large glass domes that you can reserve, other than that the tables are nestled into the trees that overlook the coast. Great drinks, great chicuterie. We went back twice and got seated at the water both times during sunset.

Roots Cafe: Unexpectedly good for being right across from the train station. Best coffee I found in Cascais, outside of a more formal sit down restaurant. Good selection of brunch food with fresh granola and avocados. One of our servers used to write software and then moved into the restaurant industry, which she described as an unusual but rewarding career pivot.

Sacolinha: Much better for coffee, orange juice, and pastries than for food. They bake their own baguettes and shortbreads that were distinctly better than the others we tried around town. Their staff seems to be good friends with the locals. While we were there one of their patrons showed up in their brand new GT, shouted for our server, and took him on a joy ride around the neighborhood. I walked away without a ride but way more caffeinated. Cash only.

We didn't have much luck in Cascais with the "white tablecloth" experiences. They were usually overpriced and packed with international tourists. I'd skip the five star dining and head to Lisbon if you're trying to eat that way. Instead, focus on the new age menus that emphasize ingredient quality. It's also easier to get a table. We got in to every restaurant we tried with no reservation and a minimal wait. But a reservation isn't a bad idea especially at Hifen.

There's a unique tradition in Portugal to serve a couvert to your table by default. Couverts vary by the restaurant but are usually some version of bread, cheese, or charcuterie. They're technically supposed to ask if you'd like it but often assume you do so they'll just bring it out anyway. If you aren't in the mood, just refuse - they won't charge you if you don't eat it, but it took us a couple times to realize that it does cost extra if you do. None of the places I listed actually had couverts, which makes me wonder whether it's an older tradition and being replaced by a younger generation of chefs.


We found Cascais to be an incredible city. The weather was ideal despite the heat wave that was gripping Europe at the time. The rave reviews also proved spot on. The people were friendly, the food was great, and it was relatively easy to establish a coworking rhythm even while working Pacific hours. I hope to be back to Portugal before long.

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