Mackenzie's Travel Unraveled

Portugal seemed like a great jumping off point for a long trip I took between jobs.  One week of my multi month adventure included enjoying Portugal. Meeting my cousin in Lisbon, we were ready for a jam-packed adventure filled with city sights, a Taylor Swift concert, and stunning coastal escapes. Here’s how it all went down—and some travel essentials I’d highly recommend for your next trip.

Exploring Lisbon with Ease

Flying into Lisbon, I’d pre-booked a private city tour through Viator. It was the perfect way to see all the major landmarks without exhausting our legs—especially since we had a concert the very next day. Packing lightweight comfortable walking shoes made a huge difference, as Lisbon’s cobblestone streets can be quite the workout.

The Taylor Swift Concert Adventure

Finding bargain floor seats for Taylor Swift’s concert felt like a win, but the event was chaotic from the get-go. My secondhand ticket never arrived, but thankfully, Stubhub’s Fan Protect Guarentee came through, just as it had years ago when they rescued me during Lollapalooza. I ended up buying a last-minute floor seat—though not next to my cousin. We switched wrist bands with strangers and enjoyed the show together thankfully. Pro tip: portable phone chargers are lifesavers when navigating unexpected situations like this.

Before even reaching the stadium, we accidentally landed at a small mom-and-pop sandwich shop bar, filled with locals in Taylor Swift outfits. A language barrier added to the adventure, but thanks to some broken English and Spanish, we connected with the friendly Portuguese crowd. Turns out, over 50 other concert-goers had made the same GPS mistake, ending up by a monument with the same name as the stadium. Having a reliable offline map or a data plan from Airalo saved can really save the day in such scenarios! While I was navigating us back, my cousin picked up her first friendship bracelet of the night!

Despite the mishaps, we arrived just in time, and the concert was absolutely magical.

Day Trips to Sintra and the Algarve

Post-concert, our journey continued to Sintra, where we soaked in the fairytale-like charm of palaces and lush gardens. Then it was down to the Algarve to bask on breathtaking beaches. A quick-dry travel towel and packable daypack were essential for our beach-hopping escapades.

Smart Travel Hacks

Thanks to Hilton Honors Points we scored accommodation in Lisbon without falling prey to the surging prices brought on by the concert crowd. Although we only had enough points for two nights—prompting a quick departure—it was worth it. Our splurge on a Lisbon tour gave us a solid taste of the city.

Final Thoughts

Portugal offered a perfect blend of music, culture, and coastal beauty. From Lisbon’s vibrant streets to the Algarve’s serene beaches, every moment was an adventure—chaotic, yes, but unforgettable. If you’re planning a similar trip, don’t forget to pack smart, stay flexible, and embrace the unexpected.

Happy travels—and may your GPS always guide you to the right place!