Day Trip to Cascais, Portugal: Sun, Seafood, and Sexy Pineapples

We left Évora and were headed straight to Sintra when Ravi (our friend from our Douro Valley adventure—remember him?) texted and said:

“I’m around! Why don’t you meander this way and let’s meet up for lunch?

It was on the way to Sintra and just made perfect sense to us. Ravi, who just happens to have a stunning beach-side place in Cascais. He walked us over to his favorite local lunch spot (literally 10 feet from the ocean), and it became instantly clear that Ravi is basically the expat mayor of Cascais. The locals love him. Our server greeted him like an old friend, and before we knew it, a gal named Allison joined the party. Allison, who also hails from California, met Ravi in their Portuguese language class.

Talk about an instant connection—we loved her right away. Not only is she beautiful, but she’s also, like, top-secret Navy Seal satellite smart, and her husband Tim is a hottie Yoga dude who is super fun, smart, and chill. I mean, she literally works with drones and satellites for the military. I’m still not entirely sure what she does, but I know it’s light years beyond my understanding. So, shout out to Allison for breaking it down into layman’s terms for us mortals. We adore you! (The boobs Allison, the boobs! Once again, if you know, well, you know.)

We spent the afternoon feasting on the freshest seafood, mouth watering bruschetta, sangria, cheese, and olives—all while soaking in an epic ocean view and even better conversation. This was shaping up to be the perfect day, and with Allison and Ravi as our tour guides, it only got better from there.

We took a leisurely stroll along the beach, checking out some of Cascais’ coolest historical spots (which included a medieval fort and the striking Citadel of Cascais, a fortress that now houses a luxury hotel and an art district). But let me just tell you about the pinnacle of the day—the Original Portugal Sexy Pineapple.

Yes, that’s what it’s called, and yes, it’s exactly what it sounds like. Imagine a giant pineapple hollowed out and filled with the most delicious Piña Colada ever, served by a “sexy” Portuguese dude. Worth every single one of the 15 Euros I forked over. No regrets.

From there, we made the mandatory gelato stop at the iconic Santini Gelato (trust me, you can’t visit Cascais without grabbing a scoop or three- Try the Passion Fruit with Vanilla). We topped the day off with a bottle of sparkling Rosé, an unreal ocean view, and, naturally, more cheese and olives. This afternoon was as exquisite as they come, and getting to share it with new friends like Ravi and Allison just made it even more meaningful.

And as if the day couldn’t get any better, Ravi—our new hero—came through with some American NyQuil. That’s right. In our state of desperate cold misery, he saved the day. It was like liquid gold. God bless America and our over-the-counter miracle drugs.

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