We have been planning this two-week vacation for quite some time. Our younger son had finally completed his five-year medical school. This will be his graduation trip present from us.
It was our first time travelling to Portugal as we have never visited the country. We decided to spend 3 nights each in Lisbon, Madeira and Porto, followed by a final 4 nights in Madrid (Spain). Taking S’pore Airlines to Rome, we had booked interconnecting European flights to these separate locations. It required a lot of planning as we had to book multiple activities and accommodations.
We set off on 02 Apr for a 12-hour flight to FCO (Rome), followed by a 2-hour connecting flight to Lisbon with a 3-hour stopover. Finally, we settled into a nice apartment near the central area by mid-afternoon after more than 19 hours of travel. We walked around the coastal area of Lisbon and decided to head to the Time Out market for drinks and finger food, which turned out to be dinner. Being jet lagged, we called it a night early.
Day 2 – Lisbon. On the next morning, we started our first GuruWalk free walking tour. It was to get an introduction to Lisbon via a 3-hour walk to see the highlights and sights. It was interesting to learn about the history of the city, and we had a good recommendation for lunch at a Portuguese restaurant serving authentic local food. We also witnessed a crime where a lady was robbed of her handphone, followed by a chase.
Day 3. For the next day, it was a full day tour to Sintra and Colares by coach bus. We arrived on a rainy morning to visit the Sintra Cascais National Park, which had beautiful and scenic sights. Then it was a quick buffet lunch to escape the rain before heading to the coast of Colare,s which was on a high cliff surrounded by huge waves for more photo taking.
Back in Lisbon, we decided to have a seafood dinner at the famous and often mentioned Cervejaria Ramiro restaurant. It was much cheaper here than back home. We chose a spider crab plus other stuff like the exotic barnacles. Very reasonable value given the high prices of seafood we are so used to.
Day 1 – Madeira. We set off on a 2-hour flight to the island of Madeira, where Cristiano Ronaldo was from. The airport was named after him. The island was about 800 square km and bigger than Singapore where you can experience the 4 seasons in one day!
We reached the very nice and modern Next Savoy hotel and dropped our luggage to walk around Funchal town. There was the CR7 museum and a small town area. We saw a convenience store that we could purchase suppies for our hikes in the next 2 days. Dinner was at a highly recommended seafood restaurant, Villa do Peixe, located in a smaller fishing village. They provided 2-way transport and we had a nice sunset (8 pm) dinner with a freshly grilled local fish, lovely fish soup and a wonderful seafood rice set for 2 with a local green/white wine.
Day 2. We went for the PR 6 and 6.1 hike, which was a total of 15 km. It was quite a long walk, and there was a common cafe resting point between the 2 routes where we refuelled and had a bite. The waterfalls were scenic, and the second one was huge with a lot of photo opportunities. After freshening up at the hotel in the late afternoon, we went searching for a dinner place and settled on a Portuguese BBQ meat place which had a good rating before calling it a night.
Day 3. The sunrise hike. We had to wake up early for a 630 am pick up, but luck was not with us. We were disappointed that we could not see the sunrise as the fog and winds were too heavy to see anything. Subsequently, they brought us to the 7 km Larano trail hike where our group of 12 followed the coastal route, which was relatively flat.
We were done by noon and went back to the hotel to chill at the pool. It had a fantastic view of the sea and the crashing waves, and we ordered lunch at the poolside. We headed to town again to experience the cable car ride to the top of Funchal in the late afternoon before heading for dinner to meet my wife’s relative for a relaxing dinner. Madeira was much better than we thought with its quality of life and vast nature offerings.
Day 1 – Porto. Had a nice walk in the morning and then a leisurely lunch by the poolside in Madeira before our 2-hour flight to Porto. Checked into our modern apartment before going for a stroll around Porto for the first time. Chanced upon a popular place with locals and tourists alike and we managed to get a table to try the famous Porto sandwich – Francesinha, a gravy-drenched bread with many types of meats (beef, ham and sausage) with a sunny-side egg on top. Also managed to narrowly miss being run over by a car at the pedestrian crossing… LOL
Day 2. Another free walking tour where we learnt about Porto’s unique history, what the rulers and kings did. Roam around town the rest of the afternoon, and visit a food market before we head to the seaside town of Matosinhos. The beach walk was refreshing, and we headed for a seafood restaurant where we ordered too much and had to pack the stuffed crab back for breakfast the next day.
Day 3. A full day Duoro Valley tour to see the famous wineries and experience what they have on offer for Port and local wines. We saw very scenic scenes of endless wine valleys followed by a short river cruise and visiting 2 wineries in between. Then we did a final walk around Porto to witness live bands performing at an open garden high above the city. Decided to try a highly rated KBBQ for dinner, which turned out to be substandard.
Day 1 – Madrid. Our 3rd time here within the last 15 years but it was our son’s first time. Our last trip here was with a group of good friends in Dec 2021 amid Covid (3.5 years ago). Visited familiar sights and went to Mercado de San Miguel for local delicacies and drinks to soak up the atmosphere. On the way back, stopover for another small bite in a nice looking corner cafe before calling it a night.
Day 2. This was the most taxing day of the trip, which I felt a bit of a hangover the morning after. We had so much food and drinks till late. Started with a morning walking tour and then a 1 pm booking at Botin, the oldest restaurant in the world (300 years anniversary in 2025). Took a rest at our apartment to watch another episode of KDrama When Life Gives You Tangerines. Then headed for the 3-hour Tapas tour at 6 pm. We met a group of French ladies in our group. After multiple drinks and tapas, we all got friendly and chatty with them and the guide. Stumbled home and knocked off like a rock.
Day 3. We had to leave at 645 am to meet for the day trip to Toledo and Segovia. It was a bit of a hangover as we had mixed drinks at the tapas tour last evening. My last drink was a whisky cocktail, bad idea… Toledo is majestic and it was the old capital of Spain before the king moved it to Madrid. It sits on a mountain top, and we now have escalators to bring us to the top before walking through it. Segovia was a pleasant surprise. The Roman aqueducts were amazing, and we walked to the castle to view the city. Came back to Madrid and had dinner at Boom Boom Ciao, a funky and colourful restaurant.
Day 4. Our final day in Madrid and a relaxing shopping day. I went for a walk in the morning to explore the area. We then had a few hours of shopping at the mall district and bought a new luggage plus a lot of clothes at Primark. We then had a popular local Spanish soup for lunch at the Teberna de la Daniela. Watched the last episode of the KDrama before heading to a place known for its paella rice sets for dinner.
The next day, we flew to FCO for an overnight stay before our 12-hour flight back home. We last stopover at FCO in 2018 and liked the place for its beach and restaurants, which was a nice stop before the long flight home. But it has changed a lot, perhaps due to COVID-19. The place looks run down now. We managed to have a nice meal under the sun with drinks before walking back – a total of about 6 km. We had our final dinner much later at 9. It was at the meat place recommended by the host, called Contro Corrente to end our vacation.
It was a pretty adventurous trip and taxing as we took a total of 7 connecting flights and spent just a few nights in so many new cities we had not been to before. We had accomplished a lot and spent quality family time with our son who will be embarking on his work career soon. It is a memorable trip that also kicks off my wife and my retirement as we move on to our next halftime journey.

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