Over 8 years ago, Anthony and I went to Europe for an epic tour. It was my first time traveling outside the U.S., and we hit 10 countries in 21 days, opening our eyes to the varied characteristics and rich history of the region. Because it was such a whirlwind, however, we vowed to return frequently, seeking additional experiences and exploring a single area in more depth. Well, more time passed than we had hoped, but we finally got to return for another overseas trip, this time visiting Portugal. We were drawn to it for its moderate climate, varied landscape and food, among other things, and we were definitely not disappointed!
We took a redeye via Newark to Lisbon and arrived around 7:30 am. Naturally, we were both a bit exhausted from travel, but luckily the hotel allowed us to have a very early check-in, so we could take a quick morning nap before starting our day. After catching a bit of sleep, we had lunch in the hotel to get plan out our first day. A light rain had greeted us, so we weren’t sure if we’d want to be out and about much, but as luck would have it, the rain let up just as we were finishing our meal and we set out on the town. Our hotel was located centrally on a main avenue, making exploration and sightseeing easy.
Because we hadn’t scheduled anything for the first day, knowing jetlag can be unpredictable, we enjoyed a leisurely, albeit grey afternoon. We loved the casual stroll without itinerary, popping into shops and exploring the main drag.
In the main square, we found a place to duck in and grab some drinks before wandering a bit more through the city as night began to fall. We happened upon a few things, including a lively market selling meats, cheeses, and goods from local artisans. Still pretty exhausted, we opted to head back to the hotel for an early bedtime.
The next morning, we awoke early, well-rested and ready to do some more exploring. With a sunnier day, we were inspired to grab some bikes and see the city in our favorite way — pedaling around town. We found a bike rental place near the city center and walked down to get our wheels for the day. The rental guy gave us some great recommendations for routes, which took us along the waterfront down to the historic neighborhood of Belém. We made a pit stop under their iconic bridge to wait out a pop-up rain shower and grab some cheap beers and crab cakes.
After the sun came back out, we continued on down the waterfront, snapping photos along the way. We turned around at Belém, where we visited an old monastery and also tried the storied Pastéis de Belém — a custard pastry made from a 100-year-old secret recipe.
During our pastry pit stop, we dodged yet another rainstorm, this one more of a downpour, which pretty much eased up as soon as we were ready to move on. As we prepared to make the return trip, we remarked on how lucky we had been in avoiding the rain fall all day. Well, I guess we jinxed it then because the skies opened up at that point and we got to ride through the rain for about a half-hour as we made our way back to the shop to return our bikes.
Thoroughly chilly and wet, we headed back to the hotel to clean up, and then hit the town again to track down some dinner. Relying on Yelp reviews, we set out towards a local restaurant with high ratings, navigating the winding hills of a nearby neighborhood. We struck out twice (one restaurant was closed and the next one we found had a very long wait) and then found a quiet Indian-themed (? I think) restaurant that overlooked the city lights.
After dinner, not quite ready to go back, we checked out Yelp and TripAdvisor again (what did people do before smartphones??) for more local haunts, and stumbled upon instructions to access a speakeasy nearby. It was a really unique experience, with some really fun drinks to serve as a nightcap before heading back to the hotel.
The next morning, we did the hotel buffet breakfast again (naturally), and then met a Lisbon local, Marta, for a private walking tour that we had previously arranged. The tour was very interesting and Marta was incredibly informative on the history and culture of Lisbon and Portugal as a whole. She walked us through some of the streets we had already been exploring, as well as many other neighborhoods, explaining the sights and answering some of the questions we had been curious about during the course of our own exploration.
In addition to providing us with some local insights and information, Marta also took us to a large marketplace to introduce us to some local foods, such as an assortment of croquettes, several different traditional desserts, local wines from the Douro region, chocolates, and a traditional cherry liqueur called Ginja. After parting ways with Marta, we returned to a shopping area that she had shown us, just off the main square, to stop in a couple of places and eventually grab some afternoon appetizers while listening to a street band playing the popular Portuguese Fado music.
After returning to the hotel for a small siesta, knowing that the Portuguese restaurants don’t even open until 7pm, we cleaned up and headed out to dinner, upon a recommendation from both Marta as well as Anthony Bourdain. We were in search of good seafood, and good seafood we received after a short wait for Ramiro, a packed joint in the Baixa neighborhood. We shared a bottle of Vinho Verde and decided we were going all out on the most recommended dishes.
Our bellies full from all the delicious shellfish, we walked back through the city and once again visited the central marketplace we had discovered on the first night. This time, we spent a bit more time there, purchasing a few souvenirs and grabbing some hot mulled wine to sip as we made our way back to the hotel.
Day four began early as we navigated Lisbon public transportation, catching a bus to the train towards the coastal town of Cascais. Once we arrived, we met up with Joao (pronounced Jah-ow), our climbing guide, for a much-anticipated trip to enjoy one of our favorite new activities. I had built up the idea of climbing in another country in my head, and this experience was everything I had dreamed of and more. As we parked on a cliff overlooking the ocean, and proceeded to make our way down to the climbing base, I knew that we were in for some fun challenges and beautiful views.
Having usually spent most of our time in the climbing gym, and on different types of rock when outside in Colorado, we were particularly challenged by the limestone. Sometimes slick and sometimes rough like lava rock, we made our ways up several different 5.9/5.10a routes, as Joao gave us some pointers on navigating some of the more technical spots. With the intense sunshine, it was the first time we actually got hot on the trip, working up a sweat as we enjoyed the amazing views. This experience, as much as I built it up, was still one of the most amazing memories of our trip.
After the climb, we wanted to visit the nearby town of Sintra, described to us by several locals as a “fairytale village.” Joao explained to us how difficult it would be to get to via public transport or taxi, so he personally delivered us to a walking trail that would get us there after a 30 minute hike. Along the way, we stopped at a lovely little crepery where we each had savory crepes from some friendly ladies, who were excited to give us more information about Sintra as well as some port-filled chocolates to send us on our way.
The walk to Sintra was beautiful and relaxing, as we stopped to take photos of castles and estates along the way.
Once we arrived in Sintra, we immediately headed straight for Quinta da Regaleira, which we had heard from several sources would be well worth a visit. “Worth it” would be a massive understatement. This property was, alone, worth the trip out to Sintra. An old estate that has changed hands and architects throughout the years, the property is filled with beautiful structures, hidden tunnels, and elaborate gardens.
One of the coolest thing that we saw was this “initiation well”, which we were able to wander down into. As we were heading down, we discovered several hidden passageways leading out to other areas within the estate. We spent some time exploring the labyrinth before exiting and taking a walking break, where we were greeted by some very friendly cats.
After we had finished at Quinta de Regaleira, we did a little bit of exploring in the “fairytale village”, and then took the train back into Lisbon. After this incredible day (climbing! beautiful views! amazing architecture! cats!), we were pretty exhausted, and actually managed to miss our stop (by several stops…) as we were heading back to the hotel, and had a bit of an adventure turning ourselves back around in the middle of the city’s rush hour, so we opted for warm showers and a relaxed (and delicious!) dinner back at the hotel.
The next morning, we packed up to leave Lisbon for the southern coastal Algarve region. After we learned how to correctly pronounce our destination city of Portimao (poot-eh-meow), we were more easily able to navigate our way down using our Eurail passes. We did run into another transportation hiccup and spent the morning hanging out in the train station waiting for our ride, but eventually we made it to the new hotel, and were greeted by a beautiful (and empty) beach. As it was the low season, the town was pretty quiet, but it made for some excellent photo ops as we enjoyed another sunny afternoon.
After a walk down the beach to explore the many rock outcroppings and take a few selfies, we stopped at one of the beachside cafe for some cocktails and seafood appetizers of shrimp and calamari. We watched as some clouds rolled in but (thankfully) luck was on our side again and the only actual weather that came along was further in on the coast and made for a beautiful double rainbow as we made our way up to the road along Praia de Rocha (Stone Beach). While there, we visited an old fortress with a great view of town, as well as a spectacular sunset over the water.
After returning to the hotel, we enjoyed a buffet dinner back at the hotel. We realized that it was Thursday — American Thanksgiving — and were amused to see that they had turkey on the buffet table alongside the seafood and traditional Portuguese dishes. After filling up on the buffet, we headed to bed.
The next morning, we took advantage of the in-room continental breakfast — which was a feast — before meeting up with another local guide for a private tour. This one, however, wouldn’t be a walking tour, and instead we were greeted outside the hotel lobby by Delfim and his sidecar.
The sidecar tour was also highly anticipated, but we had been nervous in the days leading up to it as the forecast for that day had been calling for a 90% chance of rain. It didn’t look promising even as late as the evening before, as we slept through drizzles all night, but imagine our delight as we stepped out to yet another sunny morning.
Delfim’s tour was so much fun, and once again our guide’s knowledge of the area and of Portugal were incredibly interesting. He took us to several of the neighboring towns, stopping to get out and check the (incredible) views and also getting some interesting looks from passersby.
Delfim also gave us a bit of insight into the small downtown area of Portimao, which we returned to after the tour for a bit of shopping and further exploration. We stopped at a small restaurant for lunch, where Anthony ordered grilled mackerel (a local favorite of whole fish… with eyes) and I had a traditional shellfish and rice soup, along with the usual olive appetizer. Both of our meals, while a bit strange-looking and confusing to us, were tasty.
Feeling a bit beat from the go-go-go, we headed back to the hotel for a little rest, and geared ourselves up to head out on the town that night. After getting dressed up, looking up a couple recommendations, and then hitting the street, we were met with a very dead “nightlife” scene. We couldn’t even find an appealing place to grab dinner, so we tried a couple pubs before we just decided to go back to the hotel and have a late room service “dinner”, which mainly consisted of cheese, more olives, and a huge plate of french fries, and was absolutely delicious and perfect.
Our last full day was mainly a travel day, during which we’d make our way back to Lisbon to fly out the next day. Now that we finally had the whole train thing figured out, we knew we had a few hours to kill in the morning before we needed to be at the station. After breakfast at the hotel, we headed down to the beach to watch the many surfers taking advantage of a high tide, and relax a bit on the pier.
After a few hours on the train, and grabbing a couple of fresh donuts from a train station pastry shop, we returned to Lisbon and checked back into the same hotel we had stayed in before. We walked back downtown to the Chiado district for a little bit of last-minute shopping, and were entertained to see that during our brief absence, the city had transformed for Christmas. The shopping district was bustling and there was an abundance of sparkly Christmas lights and decorations. After stopping in a couple shops, we found a local restaurant that was able to squeeze us in just as they were opening for the night, although they claimed that they were almost fully-booked with reservations. We felt like that might have been a bit of a stretch, as we were nearly the only ones there, but in any case, it lead to an incredible last meal, ranking as one of our favorites.
As we departed the restaurant, we emerged into another rainy evening, which was a fitting way to end our trip, as we had dodged so many raindrops throughout the course of the week. However, it didn’t dampen (ha!) our spirits as we made our last trek back up to the hotel. During our rainy walk, we discussed our highlights — hard to pick just one when every day was filled with something new and exciting. As far as travel, we were both surprised that we’d rank this trip high on our list of favorites, just behind our all-time favorite first trip to Europe. This time, we hope to return sooner rather than later.