Cascais:
Cascais is a wealthy suburb and Portuguese fishing village that hides some absolutely wild, rugged surfing beaches just outside of the main town. Unlike a lot of those generic beach resorts down on the southern Algarve coast that suddenly sprung up overnight to cash in on mass tourism, Cascais has been established as a premier holiday destination for generations. Yet, a ton of tourists short on vacation time only rush out here from Lisbon for a day trip.
Cascais makes for a fun day trip, but it is really best suited as a destination for an extended holiday. A single afternoon is just way too short to actually slow things down and sink into the beach groove this small village has on tap.
We are incredibly fortunate to have unlimited time on this global journey, because Cascais is exactly the type of place you rarely get the chance to plunk down for an extended stay. Missing out on that would have been a shame, because it’s such a relaxing, laid-back beach and fishing town. We allocated five full days here and felt it was the perfect amount of time to soak it all in before moving further north along the rugged west coast into the less touristy areas of Portugal.
The protected little beach coves located directly in town—like Praia da Rainha and Praia da Duquesa—are nice, mellow, and perfectly calm. But if you want to experience wild, untamed surfing beaches on par with the legendary shores of Hawaii, you’ve got to make your way about 15 kilometers outside of the town center.
[The Cascais Beach Divide]
Town Coves (Rainha/Duquesa) ──> Nice, calm, mellow, family-friendly.
Outer Coast (Guincho/Arriba) ──> Wild, rugged, massive Hawaiian-style surf.
There is a dedicated biking and jogging path that skirts the edge of the cliffs, offering panoramic views of the crashing ocean below. Barbie and I rented some bikes and rode along this scenic path, and chilled out on the sand all day. If you are a true beach lover or a surfer who appreciates world-class waves, then the outer beaches of Praia Guincho, Praia da Arriba, and Praia da Cresmina are muy perfecto.
Now, here is the major drawback. The beaches in Cascais sit on the west coast of Portugal, meaning they face the wide-open Atlantic Ocean. What does that mean in layman’s terms? It means the ocean water was cold as shit.
The hardcore surfers didn’t seem to mind because they were all wrapped up in thick neoprene wetsuits. A local told me that even during the absolute peak of the scorching summer months, the ocean water out here remains freezing cold. Because of that, I’ve got to strip some points away from the overall greatness of this place. I guess that freezing Atlantic current explains why the masses flock to the beaches on the southern Algarve coast, which sit on much warmer, comfortable waters that are actually pleasant to swim in.
The Airbnb for this stay was the absolute perfect choice. It was tucked away on a quiet, traditional village street, giving us a genuine sense of what it feels like to actually live in a real Portuguese neighborhood.
Airbnb just continues to deliver pure awesomeness for us on this trip. It is such a far superior experience to getting cooped up in a cramped, soul-less hotel room for days on end.
The absolute key to winning the Airbnb game is learning how to weed through the massive sea of options on the app, because there is always a very real potential to land yourself a lemon. I’ve read plenty of horror stories from travelers who ended up with nightmare hosts, which can easily ruin an entire vacation.
But if you look closely, those crummy experiences almost always arise when people cheap out and book the lowest-priced properties that have little to no verified reviews posted. Over the years, I’ve developed a keen eye for picking the right properties, and luckily, we’ve been hitting it completely out of the park with our selection process. That said, I’m realistic—I know it’s statistically inevitable that we’ll strike out at least once along this journey. But for now, the streak continues.
Thru the Binocs
Americans are naturally suspicious about restaurant billing, and out here in Portugal, they have a cultural quirk that would cause a literal lunchtime riot back in the States.
You sit down at every single restaurant in this country, and before you even look at a menu, the waiter immediately brings over a welcoming basket of freshly baked bread, some fresh cheese spread, and a bowl of tasty local olives. You look at it and think to yourself, Wow, what a classy, generous touch. You proceed to happily woof down the bread, slather on the cheese, eat the olives, and everything is completely cool.
You finish your delicious meal, the waiter drops the check, and boom—you look at the bottom line and realize you’ve been explicitly charged a few euros for the bread, the cheese, and the olives. Items you never actually ordered or asked for in the first place.
Lesson learned. They nailed us on that little trick the very first time we sat down in the country, but it was the absolute last time. If you try to pull that kind of unsolicited bait-and-switch stunt in an American diner, there would be an all-out war at the cash register the second the bill arrived. Consider yourself officially warned: if you don’t want to pay for the appetizers sitting on your table, tell the waiter to take them away the second they land! Next stop: moving further north up the coast!
Big Doug & Barbie Drop Out of Society 