In June of 2025, I embarked on my most ambitious and complex points-and-miles trip yet: an adults-only European getaway for me and my partner which involved nine flights in a period of just 11 days. You can read about how I booked this trip here, but in this three-part series, I’ll report out on our hotels and excursions across three destinations, starting with Lisbon.

Hotel: Hyatt Regency Lisbon

We arrived in Lisbon early in the morning after a lovely flight across the Atlantic on Iberia. We stayed two nights at the Hyatt Regency Lisbon, located in the suburb of Belém. Although Belém is about 15 minutes outside the heart of Lisbon, we really liked the quieter, calmer feel of the neighborhood. The hotel is right on the water, with stunning views of the 25 de Abril Bridge, the Golden Gate’s doppelganger. Ubers were inexpensive and easy to come by, and we found plenty of restaurants within walking distance.

The Hyatt Regency was a perfectly lovely place to sleep, but I can’t recommend eating or drinking there–not when such fantastic and affordably priced food can be found just a few blocks afield. The breakfast buffet at the hotel restaurant was certainly not worth the €30 per person that we paid on that first morning, and the rooftop bar, while beautiful, has a €25 per person minimum.

Our room was quiet, comfortable, and equipped with highly effective air conditioning, which is not a given in Europe. The property is only about two years old, and everything felt fresh and updated. My only complaint about our room is that the shower was poorly designed, or poorly sealed (or both!), and the bathroom practically flooded with every shower.

Still, as a category four Hyatt, we felt that this stay was a fantastic value and I’d wholeheartedly recommend it. It would not surprise me if this property moves up a category next year. Get it while the gettin’s good!

Excursions

I firmly believe that we stumbled upon the optimal two-day Lisbon itinerary. Our first day, we booked a half day private tuk tuk Lisbon highlights tour (scheduled for the afternoon to provide a buffer for any delays in our connecting flight from Madrid). At almost $300, this tour was the single biggest splurge of our trip, and it was worth every penny!

It was uncomfortably hot and a walking tour through the hills of Lisbon, after an overnight transatlantic flight, might have killed me. We were able to cover a lot of ground and felt like we really got a good overview of Lisbon in a very short period of time. Our tour guide was very conscientious about tailoring the tour for us, and even rearranged our itinerary so he could drop us off at our hotel at the end! 

He also pointed us toward what became a repeat dinner spot: LX Factory, a repurposed industrial building filled with restaurants, just a 15-minute walk from the Hyatt Regency. Generally, the food we had in Lisbon was cheap, very good, and vegetarian-friendly. I’d also suggest checking out Cafe Social for breakfast, and don’t miss Pastéis de Belém for the best pastel de nata in town.

The second day, we took the train from Belém about 30 minutes to the small, coastal town of Cascais. I’d thought about booking another half day tour there, but didn’t want to overschedule us; I was delighted when our tuk tuk driver told me we could just take the train! This was my favorite part of the entire trip. I can’t say enough good things about Cascais; it’s the most impossibly perfect little beach town you’ve ever seen. We had a magical day wandering through the town and enjoying the beach. Just go. You can thank me later.

Reluctantly, we said goodbye to Lisbon and Cascais and caught a TAP Portugal flight to Barcelona. Come back for part II of this series to read all about that leg of the trip!