Our Portugal adventure began with a smooth business class flight on Lufthansa, complete with Polaris lounge access in Chicago and Lufthansa Business Class Lounge access in Frankfurt. After arriving late in Lisbon, we picked up our rental car and headed south to Lagos, where we checked into the stunning Cascade Wellness Resort near dramatic cliffs and ocean views. The town’s vibrant summer energy, artistic tilework, and seaside charm quickly made it one of our favorite European destinations. A kayaking tour along the Algarve coast and visits to Camilo Beach and Ponta da Piedade were unforgettable highlights. We explored historic neighborhoods in Lisbon, sampled famous custard pastries at Pasteis de Belem, and took a day trip to the colorful Palace of Pena in Sintra. Our trip wrapped up just as Portugal’s World Cup run ended.

Day One: Arrival

We departed Chicago O’Hare around 11 p.m. and arrived in Frankfurt, Germany, close to 2 p.m. Since we booked business class tickets on Lufthansa using United MileagePlus miles, we got to enjoy the Polaris Lounge in Chicago and the Lufthansa Business Class Lounge in Frankfurt. You can read about the Polaris Lounge here and the Lufthansa Business Class Lounge here. Our layover in Frankfurt was over seven hours, so having access to the amenities of the Lufthansa Business Class Lounge was extremely helpful. We didn’t arrive in Lisbon until after 11:00 pm. Once we arrived, we walked over to the Hertz counter, and my car was ready for pickup in the adjacent parking lot. There wasn’t a line (presumably due to the late arrival), and everything was straightforward. We drove to the Holiday Inn Express, where we would spend the night before driving about three hours south to the Algarve region early the following day.

Day Two: Lagos

We arrived in Lagos around 1:00 p.m. and checked into our hotel, Cascade Wellness and Lifestyle Resort, shortly thereafter. This fantastic property is close to stunning cliffs and ocean views. Since they had a room available, they allowed us to check in early and greeted us with complimentary tropical beverages. The property has a gate leading to a walking path along the cliffs. Just for its proximity to the cliffs, this resort was worth it.

Avoid getting too close to the edge if you walk the trail along the cliffs. People have fallen to their deaths while taking selfies and lost track of the distance. The water below has jagged rocks, which can cause serious damage. Once we were done with the hike, we took a short drive to the colorful town of Lagos, about 10 minutes away.

The town of Lagos was one of my favorite small towns in all of Europe. There’s a nice vibe during the summer, and everywhere you look, you’ll see the summer colors, unique paintings, patterns on tiles, and the facades of many buildings. Painted tiles are a huge part of Portugal’s artistic history, dating back several hundred years. Other European cities incorporate it within their architecture, but none do it as effortlessly as Lagos. Even their walking paths are tiled (this can get tricky when it rains).

Several of the restaurants in Lagos offer outdoor seating, and the summer months are perfect for it. And speaking of restaurants in Lagos, there is one thing you should know when eating out. This is not a complimentary appetizer when the waiter or waitress puts bread and butter on your table. It’s common practice within the U.S. that if you are brought bread/butter, tortilla chips with dip, or anything else you didn’t order to your table before having your meal served, it’s a complimentary item you don’t pay for. If you consume the bread and butter in Lagos, it will be added to your check. If you don’t eat it, it’s omitted. They probably make a killing with thousands of tourists not knowing any better until they get their check.

Day Three: Lagos

Our third day in Lagos was one that I was really looking forward to since I had booked a kayaking tour that would allow me to kayak around the rock formations and cliffs that the Algarve region of Portugal is known for. Since my wife was well into her pregnancy at this time, she couldn’t go, so I booked the morning tour, which would also allow her to sleep in. This tour only had kayaks for two people, and both spots in the kayak had to be filled. Since I was solo, they partnered me with another person who was also solo (if you’re reading this, thanks for being a great partner, Stephanie). I highly recommend a kayaking tour if you are in the Algarve region. If you’re worried about bringing your phone on the kayak, get a waterproof pouch or bring a GoPro and a GoPro mount. The picture opportunities you will get here are postcard-worthy.

The tour takes about two hours and stops at a remote beach. You kayak with the tour guide one way, and a boat tugs everyone’s kayak back for the return trip. Wear plenty of sunscreen, as you will likely have nonstop sun exposure during the tour. Later in the day, we decided to visit the beaches in the area. The one that really stood out was Camilo Beach. Crisp, clean water, beautiful scenery, and plenty of space to lay your towel on the sand and relax. The water was much cooler than expected, but that would not deter me from getting in. If you want to get to Camilo Beach, a parking lot is available, but the spots get taken quickly. Once you park, you must walk down several flights of wooden stairs, but the views from atop are spectacular.

Once we had wrapped up our day at the beach, we stopped by the town of Lagos for dinner and then returned to the hotel to prepare for the following day.

Day Four: Lagos and Lisbon

Our rental car was due for return at the Hertz at Lisbon Airport by 10 pm. This gave us the morning and early afternoon to check out the rock formations of Ponta da Piedade in Lagos. There is a parking lot that can fit many cars (though it will likely fill up fast during peak season), and you can take several flights of stairs down near the water.

I decided to hike up one of the “mini peaks.” There is only room for 3-4 people, but the views are worth it.

Ponta da Piedade was our final stop in the Algarve region of Portugal. Now, it was time to drive north to Lisbon and explore that beautiful city.

Lisbon

When we arrived in Lisbon later that afternoon, there were overcast skies and a few ominous-looking clouds. We thought it would be a pretty blah day. Fortunately, the clouds moved on, and there was sunshine just a few hours after we checked into our hotel. Using IHG points, we stayed at the Intercontinental Lisbon, a splendid hotel in a central location only 10 minutes away from Baixa and the Moorish Quarter.

There is no better way to get a flavor for a city than doing it on your feet. We walked on Av. da Liberdade and just kept going and going.  The further we went towards the shopping district, the more it felt like the Las Ramblas area of Barcelona, Spain. Since the World Cup was ongoing and Portugal was still alive (this would change in a few days), there was a vibrant and festive atmosphere no matter where you turned in Lisbon.

While walking through Av. da Liberdade, we took a few turns, leading us to a trendy shopping area called Baixa. This neighborhood had excellent shopping, dining, and chic hotels and lounges.

We found a hotel called Hotel do Chiado. On the 8th floor, they had a rooftop lounge called Entrentato. No reservations were needed, and there was plenty of seating available. The views of the city and the red terracotta roofs were excellent.

If you find yourself in this area, check out Entretanto. Baixa also has a historic elevator called the Santa Justa Lift, which you can experience for 5.30 euros. It takes you to the top and gives you panoramic city views from a slightly different perspective. We did not do this since the wait time was over an hour, and the rooftop lounge provided the views we sought.

Day Five: Lisbon

The first thing on the agenda for today was going to Pasteis de Belem, famous for its custard pastries. You will find imitators throughout Lisbon, but this place is the original. They’ve been churning out their renowned custard pastries since 1837. If you come to Lisbon, you cannot leave without visiting this place. You just can’t.

Once we were done eating, we took a walk around the area to see some interesting points of interest. First among them was Jeronimos Monastery. Construction on this building started in 1501 and was not finished until about 100 years later. If you’re into Gothic architecture, this building is a classic example of Portuguese Gothic architecture found all over Lisbon. Jeronimos Monastery is a UNESCO World Heritage Site.

After walking around Belem, we took a 15-minute Uber ride to the neighborhood of Bairro Alto upon the recommendation of locals. Bairro Alto is known for its sloping, cobblestone streets, tiled buildings, and colorful facades.

This quarter of the city was one of my favorites and really what I envisioned Lisbon to be. It had a unique charm and felt like it wasn’t trafficked by as many tourists as Baixa and Belem. There were plenty of cafes, restaurants, and local shops. Walking was easy going downhill, but uphill was occasionally a struggle. Your best bet is to walk downhill and take the trolley going back up.

As we kept walking, we recognized some places we had been to the day before. We didn’t realize initially that Baixa was adjacent to Bairro Alto.

Many Portuguese restaurants in Lisbon serve ceviche, raw fish cured with citrus juices and spiced with peppers and other seasonings. Since this was my first trip to Portugal, I didn’t want to risk ruining my stomach, so I avoided ceviche, but it is a local favorite.

Day Six: Sintra and Lisbon

Sintra is a small town about a 45-minute Uber ride from Lisbon and is home to the Palace of Pena. If you’re in Lisbon, I highly recommend visiting this part of Portugal and experiencing the Palace of Pena. It is a UNESCO World Heritage Site and was completed in 1854. It served as the home for Portuguese royalty until the late 19th century and was converted into a museum in 1910. The Palace of Pena has a facade of vivid colors and architecture that incorporates Romanticism, Neo-Gothic, and Neo-Renaissance. If you visit, I highly recommend not driving to Sintra!  The roads are narrow, and parking is almost nonexistent. Uber or a Taxi will drop you off near the ticketing office. You can do so from the ticket windows if you haven’t purchased your tickets online. Tickets to the Palace of Pena cost 14 euros for adults and 12.50 euros for children and seniors.  From there, you can take the arduous 1 km hike to the castle or pay 3 euros for the shuttle. We took the shuttle, and I don’t regret that decision. Everyone we saw walking up the hill looked winded and tired.

They also have a cafe and a souvenir shop on the premises. You should budget at least 2 hours here and possibly more if you’re detail-oriented. Outside on the Arches Yard, you get a beautiful panoramic view of Sintra and other points of interest, such as the Moorish Castle.

When you exit the Palace of Pena, you take the same shuttle that brought you there. It will drop you off near the ticketing area. The shuttle runs once every 15-20 minutes. Cars are not allowed to pick up passengers in this area. To get to the town of Sintra below, we paid 10 euros for a ride on a tuk-tuk. Sintra is a small, quaint town with nice restaurants, cafes, shops, and nice vibes.

We walked around Sintra until evening and then took an Uber ride back to Lisbon. Portugal’s soccer match against Uruguay would start shortly, and we did not want to miss the various viewing parties throughout Lisbon.

Lisbon

At this point, Portugal was down 2-1 to Uruguay, and you can see the consternation on the faces of many fans of Portugal as the clock keeps ticking away. I wanted Portugal to win badly to witness the euphoria of fans who live and die with soccer yearly. It just wasn’t meant to be, and the atmosphere around Lisbon went from festive to somber as the final seconds ticked off the clock. The build-up leading up to this game was incredible, and witnessing fans slam tables, curse at the TV, and explain to their friends why Portugal sucked, I knew exactly what they were going through. It was comforting to know that the same behavior I exhibit when the Bears, Bulls, Blackhawks, or Cubs are playing terribly is universally practiced. Once the game ended, my wife and I got dinner and called it a night. Our flight back to the U.S. was early the following day, so getting sleep was definitely on our minds. This concluded our memorable trip to Portugal.

Recap

We tried to fit in as much as possible during our six days in Portugal.  Although we didn’t get to visit it this time, we hope to see the city of Porto next time we visit Portugal. For us, it came down to Lisbon plus the Algarve or Porto. Since there would have been some overlap between Porto and Lisbon, both being proper cities, we decided to skip Porto this time and visit a region that was completely different from either. Lisbon and the Algarve have not been overrun by tourists like London, Barcelona, Amsterdam, and Rome. If you plan to go, do it before Europe’s best-kept secret is no longer a secret. If you thought this itinerary was helpful, please subscribe for alerts on additional itineraries, both domestic and international.