Itinerary
Lagos (Algarve) –> Madeira –> Lisbon
I owe the inspiration behind this trip to Athea, who had read up on Portugal after seeing it on a “best places to travel in May” list. Originally, the plan had also been to head up north to Porto and do some touring there, but we were stuck for a couple extra days in Madeira – due to high winds and their small runway, we ended up having to stay a couple days, meaning we could only visit Lisbon after returning to the mainland.
Writing this in my third week of overseas COVID quarantine in 2021, in retrospect, it’s quite funny how stressed out we were about two days of delays in returning home from Madeira – with overseas flights and all. Crazy how perspective changes things.
Lagos / Algarve
After landing at the Faro airport, we drove our rental car down to a beautiful B&B in Lagos, which is pretty much the gateway to the Algarve region. “Algarve” from “the West” in Arabic, dating from the times when the Iberian peninsula was under Moorish rule. The area is known for its fantastic weather, beaches, and oceanside cliffs and sea stacks that make perfect opportunities for long hikes. We spent 3 days here, going on about 20 miles of hikes up and down the sea cliff formations, and taking a boat tour inside the incredible Benagil Cave.
Sea Stacks Galore 
Benagil Cave
Madeira
After Algarve we headed down to the island of Madeira, a volcanic Atlantic island that is part of Portugal, following the path of the first settlers (albeit a bit faster). Although Madeira was known in antiquity, it was first settled by Portugal in the early fifteenth century. Today, it is a highly populated and crowded island – and, in my small rental car, one of the most terrifying places I have ever driven in my life. (Eklutna road following an ice storm is my first).
The first full day in Madeira, we headed up about 6000 feet to do one of the most incredible hikes I have ever done in my life – a traverse between the two highest points on Madeira, Pico Arieiro to Pico Ruivo. The height of these mountains in relation to the small size of this island was incredible to me, and the views from the top were expansive and beautiful. The slight breeze was enough to swirl the clouds below us, but not bad enough to affect the experience. At only 8 miles, it also left us worked out, but with plenty of energy for the following days.
On the Pico Ruivo summit 
Above the clouds
The next day we went scuba diving on the south of the island. While scuba diving off Madeira is supposed to be pretty great, there is only one word to describe our experience – COLD! We were diving in May, when the Atlantic is still warming – the best times to dive are later in the summer, for both comfort and viewing sea life. Still, always good to get out and work on diving basics. Alaska diving is a no-go for me, I’m already cold enough on land.
The next day we set off on an epic mountain bike ride – which was definitely had the largest elevation loss of any bike ride I have ever done, at ~5000 ft. We took a shuttle up to around 4500′, and then biked up to the hike point, which helped warm up the muscles. What followed was an incredible ride through flowy singletrack, which had technical sections but also “bailout” sections that skipped some of the gnarlier points. After descending about 2500′ on the single track, we rode “side-hill” horizontally across the island on levadas – historic irrigation canals that are still used today to direct water for agricultural uses. The levadas, primarily made from concrete, form a single-track wide path that is coincidentally perfect for mountain biking.
The final part of the ride was an absolute rip down steep pavement, an incredible adrenaline rush as we tore down the streets with the ocean shimmering below. This capped off what was without a doubt one of the best mountain biking experiences of my life.
Prepping to ride single track 
Road biking back into town
We were thankful to have had a great time in the few days we had planned to be here, because the next two days were spent primarily in the airport as we waited on multiple flight delays. It reminded of the several times I’ve been stuck on the North Slope, waiting on weather to clear up so I could go home. After two days wasted at the airport, we were finally able to get out and make it to Lisbon.
Lisbon
And it was worth the wait! What an incredible, safe, clean city to visit. I was shocked when we were walking through the old city and came across Roman ruins – a testament to the expanse of this empire, especially considering the Roman ruins we had encountered in Jordan less than a year before.
Although our time in Lisbon seemed to me to be as much about sampling great food and strolling around as anything else, there were three main highlights for me:
1) Belem Tower: a picturesque defense tower set out in the ocean, which to me was representation of what Lisbon represents: the birthplace of deep sea navigation, possibly the greatest development made to shape the modern world.
2) Praca do Comercio: so far, my favorite city square I have ever seen in Europe. sprawling, surrounded by beautiful architecture on all sides, and not too crowded.
3) Castelo de Sao Jorge: a Medieval hilltop castle that provides unparalleled views of the city’s orange-roofed buildings.
Belem Tower
Praca do Comercio 
View from Castelo de Sao Jorge
Portugal was a friendly, progressive country, and I have to agree with its spot on the “Best Places to travel in May” list. I hope to be able to return one day to visit Porto and Sintra – and also the Azores, after our amazing time in Madeira.