Mistakes We Made Traveling to Portugal for 2 Weeks; Biggest Regrets

My husband and I recently spent two weeks in Portugal. We had a great time, ate fantastic food, and drank a lot of wine, but it was also our least favorite European vacation to date.

As outdoorsy travelers, we missed the hiking and adventure activities we usually prioritize. We also made some planning and packing mistakes that affected the trip.

Arriving later in the day would’ve been better

On past European trips, we always had a plan for our luggage after landing, whether that meant a rental car, late arrival, or early hotel check-in.

Our Portugal flight got in at 9:45 a.m., and we were heading straight to Porto, no rental car. But we were renting an apartment with no front desk and no flexibility on check-in time.

That meant we were stuck carrying our luggage for hours before the housekeepers could store it, and we couldn’t nap until nearly dinner.

We stayed in Lisbon too long

Usually, we spend a couple of nights in a city and use it as a home base to visit nearby wilderness areas and smaller towns.

At the urging of our friends — who are big foodies and love getting lost in cities — we decided we’d try a more metropolitan-focused vacation in Portugal.

We stayed in Lisbon for four nights. For us, that was two nights too many. The city has plenty to offer, but much of our sightseeing felt obligatory.

We loved exploring São Jorge Castle and took an amazing food tour in the Alfama neighborhood, but otherwise, we found Lisbon’s streets were packed with tourists shuffling from one landmark to another.

Worse, in some crowded parts of town, we were regularly offered drugs by random strangers, often in front of families with kids. And unfortunately, during our visit, many of the museums were closed for restoration — important work, but unlucky timing.

I wish we’d spent more time in the Douro Valley, the Algarve, and nearby small towns

The Douro Valley is the most beautiful wine country I’ve seen, far better than Napa, Tuscany, and Germany’s Mosel Valley.

We took multiple wine tours over two days, but we barely scratched the surface of what this region has to offer. While here, we only toured two small towns — Amarante and Pinhão — but there was so much more to see.

We stayed in Carvoeiro in the Algarve and used it as a base for exploring nearby towns, a zoo, and a sea-kayaking tour at Benagil Beach, but honestly, I could’ve used another couple of days planted on the beach with a good book.

Most regrettably, we didn’t dedicate much time to hiking in Portugal.

Sure, we walked portions of the Seven Hanging Valleys Trail (a coastal hike along the Algarve coast), but we completely missed Peneda-Gerês National Park, which offers amazing hiking amid lush forests, cascading waterfalls, and rolling mountains.

We shouldn’t have booked a car

For the most part, we relied on public transportation in Portugal. Although every train we took ran a bit late and we had to hire a private driver one day because of a strike, I think renting a car is a mistake.

We’d booked a car for the final leg of our journey, the Algarve, so we could travel to all the small coastal towns. But a day before we were due to pick it up, we canceled the reservation — for two reasons.

First: Throughout our trip, I saw firsthand why Portugal’s considered among the most dangerous countries to drive in. I’ve driven in six other European countries and felt confident, but watching the brazen, wild maneuvers some local drivers pulled had me thinking twice about getting behind the wheel.

Second: Rideshares were reliable and affordable in Portugal. We saved money by Ubering around the Algarve instead of renting a car and paying for fuel, and we had no problems getting anywhere we wanted to go.

This is one mistake I’m glad we ultimately avoided, but it was still stressful to cancel the car and book train tickets at the last minute when we changed plans.

Somehow, we made rookie packing mistakes

My husband and I pride ourselves on our packing abilities. Even on monthlong trips, we don’t check a bag. We cram our lives into two backpacks and two carry-ons, which makes train travel and walking through European streets easier.

But we made some major packing mistakes in Portugal. First, I packed running shoes and resistance bands because I planned to keep exercising on vacation. I didn’t use them once.

Portugal’s hills and our packed itinerary provided more than enough exercise. For the entire trip, those shoes and bands took up space we could have used for more clothes (we had to do laundry twice).

We also forgot to pack American cold medicine, a lesson we learned years ago on our international travels, but completely forgot. And of course, I got sick near the end of the trip.

We got medicine from the pharmacy, but it was more expensive than American meds, and, in my opinion, European meds are often not as effective.

For context, the medication a pharmacist ended up selling me was single-ingredient, only targeting pain and fever. My go-to cold medicine back home is a combination drug that tackles multiple symptoms, including nasal congestion, cough, pain, and fever. I definitely wish I’d had it with me.

Unaccustomed to prioritizing museums and dining over hiking, we also packed way too many “fancy” outfits. Of all the European countries we’ve visited, Portugal seemed to have the most laid-back attire, even at nice restaurants.

We would’ve been fine with a couple of polos and a pair of dressy shorts each.

Despite the mistakes, we had a great time — and will course-correct on next year’s trip

We loved our time in Portugal. The people were so friendly, the architecture and landscapes were stunning, and the food was delicious.

We just needed to do a little more research and better planning. For our next trip, we’ll take what we learned and adjust the itinerary to better meet our needs.