For three weeks in mid-November and early December 2021, Spain and Portugal were my destinations for my daily work at Leadtail while offering wondrous places to explore and visit. There is something deeply satisfying about being productive with meaningful work while at the same time looking up from my laptop and seeing a new country or airport before me. As luck would have it, Leadtail enables me to work from anywhere so long as I have access to WiFi.

Working From Anywhere but Home

In 2019, before COVID, I was fortunate enough to visit Denmark, Sweden, Norway, and Iceland and later traveled to Japan, Taiwan, South Korea, and China before the end of the year. I was supposed to travel to Dubai, Istanbul, Lisbon, Milan, and London in early 2020, but it got canceled. COVID has impacted everyone, and my canceled and delayed trips are a mere inconvenience, but being able to get away again was a relief.  Little did I know that Omicron would be a thing in only a week – so my timing for getting away at this moment was ideal.

After two years, traveling again!

Now, finally, on November 19, I found myself at PDX airport, where after getting past security, I made my way to the crowded Alaska Airlines lounge. With sparse food offerings and masked people milling about, I grabbed a coffee and sat down at the counter facing the tarmac, opened my laptop, and got to work for a few hours before boarding my flight.

Here I was working on my usual client tasks about to embark on a 3-week journey to Spain and Portugal, where each day included 2 – 9 hours of remote work. I always enjoyed working in airport business lounges or at empty gates, Airbnb’s, coffee shops, and train stations. It felt good being productive while also being excited to start this long-awaited trip to new places on my lengthy list of global destinations. I typically prefer to visit a few countries and cities during each trip, but this time it was only two countries and four cities due to the PCR testing needed to enter each country.

Finding the best deals

Before booking my trips, I search for the best deals across many platforms and travel apps. For long-haul flights, I always try to find the cheapest business class seats. The trick is to be flexible on departure and return dates, as well as arrival and departure cities. Once I have the flight itinerary booked, I locate Airbnbs close to where I want to be. For example, in Madrid, Porto, and Lisbon, I chose to be within short walking distance to the main train stations. On this trip, I booked single apartments with full amenities including much-needed clothes washers. These places were located in nice areas that were cheap or modestly priced, comfortable, and ideal for remote work.

Portland to Barcelona via Chicago and Lisbon

After a couple of hours managing client activities, I boarded the Alaska Airlines 737 flight to Chicago, where I had a four-hour layover before getting on a TAP Portugal A330-neo to Lisbon. It had been a few years since I had been in O’Hare, and unfortunately, the international terminal was a disappointment. The departure hall looked old and tattered, and the windowless departure gate for TAP had several ripped seats, which was sad. The business lounge for TAP passengers was also closed, so I bought a sandwich and made do until we boarded our flight.


The business class product on TAP was good, but the crew was not as friendly as other airlines. Arriving in Lisbon (above) was scenic and beautiful as we flew over the Tegus River, descending over Portugal’s capital city. I had another six-hour layover before heading to Barcelona. After going through customs and showing the QR code for my COVID PCR test, I made my way to the TAP business lounge, ate some food, and worked away.

The flight to Barcelona was short and efficient – I made my way out of the airport and hopped a shuttle bus to the airport hotel I had booked for the night. It was perfect for a shower and then off to bed as I was exhausted. The next day, I Ubered into the city and found my Airbnb, which allowed me to drop off my bags before checking in later that afternoon.

Pocket WiFi makes traveling easy

The night before, I had a pocket WiFi waiting for me at the hotel from Spain Internet. These little portable devices are perfect for connecting with your phone and laptop, so I have Internet wherever I go. Since leaving Portland, my phone has remained on Airplane mode as I only link to WiFi. As a result, I avoid the AT&T $10 per day international fee. The pocket WiFi was only $50 for eight days in Spain and $62 for 14 days in Portugal. Absolutely worth it!

Barcelona super cool balcony

The first thing after arriving in Barcelona was adjusting to the nine hours difference in time. It took a couple of days to get sorted, and the new routine of working in the evenings with some meetings running past 11:00 PM. I would still find myself working in the mornings before heading out and exploring the city and the Mediterranean Sea. The Airbnb in Barcelona was cool in that it had an enclosed balcony overlooking the street below. I immediately loved this feature as I watched the busy street scene below me whenever I looked up from my screen.

Snow in Spain?

After a few amazing days in Barcelona, I was off to Madrid by high-speed rail. Watching the Spanish countryside pass by was fantastic. At one point, we were high enough to see snow on the ground which was a surprise. Arriving in Madrid was easy as I disembarked from the train and walked 20 minutes to my Airbnb.

Saying hello to our colleague in Madrid!

Part of the reason for coming here was to meet our colleague, Corina Manea, who lives outside of the city and had joined Leadtail in February 2020. It was great to meet up with Corina “in real life” after almost two years of communicating via BlueJeans and Slack. We had some lunch and walked up parts of Gran Via and Puerto de Sol before she grabbed an Uber home. Before I knew it, we were back on Slack.

PCR testing – the new norm in international travel

After a few days of touring around scenic Madrid, I went for another COVID PCR test before my flight to Porto. The cost (ranging from $90 – $200) and the time needed to get these tests are one of the drawbacks of traveling during COVID, but it will probably be the norm for some time.

Madrid’s airport is modern, spacious, and proved to be ideal for getting some work done before my quick flight into Porto. The Airbnb arranged to have a driver meet at the airport, but I got off the plane and through the terminal so quickly, that I was the one waiting for my driver instead of him waiting for me with a sign that had my name on it.

Charming Porto 

Arriving at my Airbnb was fantastic! It was a modern 1-bedroom apartment built in a 300+-year-old building with a stone frame. It was the perfect mix of comfort and practical space for working for a week.

Porto was by far the most interesting and scenic place to visit on my trip. The magnificent Dom Luís I Bridge dominates the city along the Douro River that features colorful old buildings along its banks. The city is small enough to get around with ease and large enough to have great restaurants and amazing sights. Seeing the Atlantic was thrilling on a beautiful sunny day and the perfect way to spend a few hours before my evening client meetings.

Portugal’s beautiful countryside

The six days I explored and enjoyed Porto went by too quickly as I would have loved to stay longer. So much to see and do! Next up was my train journey down to Lisbon. I had intended to take the high-speed train direct but booked the slower train that made stops along the way due to timing. Wow, I couldn’t keep my eyes off the landscape and the old train stations covered in tiles. At one point, I had tried to work with my laptop open and ready, but I was too distracted by the wonders of Portugal.

Busy Lisbon

Pulling into the Santa Apolónia train station in Lisbon left me with a quick 15-minute walk to my final Airbnb. What a great way to start the end my 3-week journey with the most scenic and comfortable accommodation! I had a balcony overlooking restaurants below and the 12th century Lisbon cathedral above five floors up. It was breathtaking every time I stepped out. After getting settled in, I made my way to Praça do Comércio, Lisbon’s main square on the Tegus River. It was Saturday evening, and the place was jammed-packed with tourists. I tend to look for areas with few if any tourists, so for this moment, I walked through the crowds at my usual breakneck speed and vowed to return the following day. As I had hoped, the following morning was perfect as the square, and the once busy streets were now empty. I can see why Lisbon is crowded. It’s beautiful and offers a lot of incredible historical sights.

Magical Sintra 

I decided to make the most of getting to and from Sintra, the UNESCO World Heritage site about 35 minutes north of Lisbon, by booking a day tour. All I can say is WOW! If you ever visit Lisbon, don’t miss Sintra. Words can’t describe just how amazing this place is. Our guide took us around the town and the grounds of Quinta da Regaleira with its famous inverted tower. After a sumptuous lunch of grilled cod baccala, we headed to the coast, first to a sandy beach flanked by cliffs with caves, and later to the westernmost part of mainland Europe. Spectacular scenery at every turn.

Early morning lone tourist

As previously mentioned, large crowds of tourists are not my thing, so getting up early and heading out to the most popular sites was what I did and to my delight, found these attractions were empty. One morning before 7:00 AM, I hopped on a tram filled with Lisboner’s heading to work. I suspect I was the only “tourist” on this 25-minute tram ride out to see the Jerónimos Monastery, the Padrão dos Descobrimentos, and Belém Tower. No one in sight and a beautiful sunrise over the Ponte 25 de Abril bridge and Christ the Redeemer. To see the folks heading to work made me thankful that I no longer deal with the hassle of commuting. I haven’t owned a car in three years. All hail Uber/Lyft!

The flight to Canada

After another COVID PCR test the day before leaving, I was back at Lisbon’s airport in the TAP lounge working away before my flight to Toronto and then onto Vancouver. This was now December 11 and with Omicron rapidly spreading, I was to be subjected to another PCR test upon arrival in Toronto. The flight on the A321neo was probably the best of the business class seats, having an entire “row” to myself on this single-aisle plane with a two-one-two seat configuration. Comfortable and spacious. My flight from Toronto to Vancouver was on a Boeing-787, and the Signature Class seats were excellent – but not quite as comfortable as TAPs A321-neo. (BTW – the best business class seat I have flown with is EVA Air). After eating and catching up on work in the Air Canada lounge, our delayed flight to Vancouver finally made it to my hometown, and I hopped the Canada Line into town.

Why Leadtail makes work FUN!

Now, after more than five years at Leadtail, my experience has been nothing short of incredible. To see the growth of this start-up from three people to approaching 30 is a testament to Carter Hostelley and Karri Carlson’s vision, persistence, and sheer determination. The foundation of Leadtail is based on integrity, honesty, and transparency, which is easy for some organizations to claim but rarely does one find any business that lives by these principles daily. All of this is possible because of the work we do at Leadtail. It is a privilege to work with such a dedicated group of people! No company has ever come close to what we do here during my career.

Working remotely in a foreign country, I find peace and solitude mixed with adventure and wonder. It’s a great combination when nothing is pressing back home, so despite COVID, I hope to continue my adventures in 2022. As of this writing, I am still in Vancouver and will be returning to Portland on Jan 6 – after 49 days – only to start planning my next get-away.

This article was originally published on LinkedIn.