A Jet Set Roulette Adventure: Kimmie's Bucket List Journey to Portugal

This year, I embraced the spirit of adventure in the most unexpected way—through a Jet Set Roulette trip that led me to the enchanting country of Portugal. The lead-up to this journey was nothing short of chaotic, but that was part of the fun. With no plans, no guide, and a commitment to total spontaneity, we set out to see where the world would take us.

After hopping from counter to counter at various airlines, we quickly learned that spontaneity doesn’t always go as planned. United Airlines no longer sells tickets at the desk, Delta Airlines was fully booked thanks to fog, and JetBlue took so long to process our booking that we missed the flight entirely. It was pure chaos, but we couldn’t help laughing at how ridiculous it all was. Eventually, we made it to LAX, then JFK, and chose the warmest European destination available: Lisbon. And just like that, our adventure began.

Lisbon: A Whirlwind Arrival

Our first stop was Lisbon, where the cobblestone streets and pastel-hued buildings welcomed us with open arms. The city was alive with holiday magic, and every corner seemed to hold a story. From iconic tram rides to soaking in the festive lights that adorned every street, Lisbon at Christmas was nothing short of enchanting.

As someone with a gluten allergy, I didn’t get to try the famous pasteis de nata, but the food scene still amazed me. I ventured into seafood territory—something I don’t typically eat—and was blown away. The fish was so fresh and flavorful that I couldn’t get enough. Another standout meal was at a 45-year-old Spanish tapas restaurant, where every dish was so simple yet unforgettable.

Lisbon’s charm wasn’t just in its food or streets—it was in the people. Everyone we met spoke fluent English (and multiple other languages) and welcomed us with genuine warmth. Add in $1 espresso shots and how affordable everything was, and Lisbon quickly became a city I didn’t want to leave.

Porto: A Toast to Wine and Wellness

From Lisbon, we rented a car and road-tripped to Porto, and let me tell you, Porto completely exceeded my expectations. Sure, everyone talks about how beautiful it is, but you have to see it to really get it. It’s not just the colorful tiled buildings stacked on rolling hills or the way everything leads down to the shimmering Douro River. It’s the whole experience: the food, the wine, the charm—it’s all next level.

Let’s talk about the wine first because, honestly, Porto makes Napa feel kind of basic (in the best way). We visited a winery where they had port aging for over 100 years—walking into that cellar was like stepping back in time. But my favorite moment? Trying a local friend’s unlabeled, homegrown port wine. It was phenomenal—so smooth and rich that it put a lot of “fancy” wines to shame.

We also hopped on one of the iconic boat tours along the Douro River. They use replicas of the ships that once transported barrels of wine, and cruising down the river, surrounded by steep hills of terraced vineyards, is an experience that just stays with you. And the Douro Valley itself? Magic. The views, the air, the timelessness of it all—it’s one of those places that makes you stop and just breathe.

Madeira: A Bucket-List Must

While we were in Lisbon, a local told us, “You can’t leave Portugal without seeing Madeira.” In the spirit of adventure, we booked the flight right then and there, not knowing Madeira is one of the most dangerous places in the world to land. Thankfully, we learned that little fact after we arrived safely! The pilots were incredible, and everything went off without a hitch.

Madeira itself is otherworldly. One moment, you’re on a tropical beach with crystal-clear water, and 20 minutes later, you’re up in the mountains surrounded by cedar trees, wild goats, and cows. It’s like being in Hawaii and Colorado all at once.

The Fanal Forest was a standout for me. The trees there are close to 1,000 years old, and walking through that misty, ancient forest felt like stepping into a fairytale. It’s the kind of place where you half expect magical creatures to pop out from behind the trees.

And then there was New Year’s Eve. Madeira’s fireworks are world-famous for a reason. Standing by the ocean, watching fireworks light up the sky and the entire island, was an unforgettable way to ring in the new year. It was pure magic and the perfect ending to an already incredible trip.

The Magic of Jet Set Roulette

Looking back, this trip was everything I didn’t know I needed. From the festive charm of Lisbon to the timeless beauty of Porto and the surreal landscapes of Madeira, every part of this journey felt like an adventure.

Jet Set Roulette is not for the faint of heart, but that’s what makes it so special. The unpredictability, the spontaneity—it’s freeing in a way I’ve never experienced before. If you’re thinking about doing something like this, my advice is to try it during the off-season to save some money, but honestly, everyone needs at least one trip like this in their lifetime. I’ve never felt more free, more refreshed, or more alive.

Cheers to new beginnings, radiant skin, and unforgettable memories!