I also wish I'd planned more day trips and prioritized the things I really wanted to see.
This year, it felt like everyone I knew was visiting Portugal — which makes sense, considering the country saw a record-breaking number of tourists between January and June.
So, I was excited to see what all the fuss was about when my boyfriend and I finally made our way there this summer.
I hadn't put much effort into our last vacation together, so I was determined to make this trip different.
After weeks of patient monitoring, I found great flights, my spreadsheet was magnificently organized with activities, and I booked awesome accommodations.
But even with the most diligent planning skills and luxe accommodations, no vacation is perfect. If I were to do it all over again, here are a few things I'd do differently.
I would make more dinner reservations in advance.After our first night in Porto, we started making lunch and dinner reservations at breakfast.
Rebecca Strassberg
Despite staying right outside the Ribeira and Baixa neighborhoods, where restaurant choices abound, we still found dinner reservations difficult to come by if we waited too long.
On our first night in Porto, we gave up a reservation at The Door, a trendy tapas spot. But we didn't realize that the restaurant would be booked for the rest of our time in the city.
We settled for wherever would feed us at 9 p.m. and eventually started making lunch and dinner reservations over breakfast.
Staying in a more central part of Lagos would've made that leg of the trip more relaxing. It only took us 25 minutes to walk to the beach, but it felt much longer.
Rebecca Strassberg
When planning our trip, I didn't have a preference where we ended up in the Faro District, Portugal's southernmost region. I just wanted a beach, and Lagos was familiar.
I agonized over where we would stay in Lagos — but for the wrong reasons. I was so concentrated on stars and reviews that I neglected one of the biggest factors: location.
The Airbnb I booked was wonderful. As a New Yorker, I wasn't even intimidated by Google Maps' projected 12-minute walk to Old Town Lagos and 25-minute walk to the beach.
What I didn't account for, however, was how incredibly steep Lagos is and how sore my calves would be.
Porto had been hilly and full of 15,000-step days, historic churches, and museums — and Lisbon would be more of the same — so I banked on Lagos being the relaxing stint of the trip.
Unfortunately, I never did get that break I was hoping for. A mile-long walk to the beach on vacation feels like five. And climbing up a hill after dinner makes it feel like a mountain.
However, we had a much better time at our accommodation in Porto, Casa da Companhia, Vignette Collection. This five-star IHG hotel offered complimentary breakfast and was located in a central location that made exploring the area simple.
I'd prioritize seeing more of the things that make Portugal special.I wish I had made time to visit Capela dos Ossos.
saiko3p/Shutterstock
It can feel intimidating to dedicate an entire day to just one thing, specifically on a multicity trip. However, I wish I'd prioritized the things that make Portugal, Portugal.
For example, I've wanted to visit Capela dos Ossos (Chapel of Bones) in Évora for years. It was only an hour and a half drive from Lisbon, but we didn't end up going.
And even though Porto is world-famous for its production of port (fortified Portuguese wine), we skipped a day trip to the Douro Valley. Although we drank port and toured a few distilleries in the city itself, an excursion would have cemented that leg of the trip.
After all, at the end of the day, a short car ride is nothing compared to an eight-hour flight.