Our trip to Lisbon started with a dress rehearsal for travel when we are old farts. We got to the airport 5 hours before our flight left. This was 4.5 hours later than I would have arrived in my twenties 🙂 It was partly getting-older-anxiety but mostly a question of logistics. Craig and Sara were meeting us enroute so that Craig could drive the car back to Huntsville. A couple of extra hours in the airport didn’t feel like too big of a deal to save ourselves a lot of rigamarole. 

Just as we got to the airport the wheels on both of Rob’s suitcases finally did what they have been threatening to do for a long time – stopped working. Instead of rolling the two beasts he had to drag them along like a two year old having a tantrum.  

Considering we are going to be living and working in Europe for over two months, I think we have done admirably well to get all of our stuff into two suitcases each. I have my traveling kitchen essentials as well as core worky-work supplies like notebooks and binders. Rob has his portable stand up desk system. And then there are the shoes. We’re straddling end of summer weather and eventually getting into early winter. I like to keep the unlikely option open that I am going to be running 🙂 We’ll definitely be hiking. And we’re in all these amazing European cities and I want to look fashionable… That adds up to a lot of footwear. 

So even though I feel like we should get a minimalist badge of honor for honing it down to fit into bags that the two of us can roll (or drag) through airports – it’s quite a bit to manage. We found seats as close as we could to our check in desk and settled down to wait for them to open. (I told you we were early!)

Considering all the stories about the horrendous line-ups and wait times at the Toronto airport, our experience was incredibly smooth. I suppose being first in line to drop our bags off helped 🙂 Security was quick and easy. We had lots of time to have a few leisurely games of cribbage while I sipped on a glass of wine and Rob a beer beside our gate. Very civilized. 

Our flight was supposed to leave at 11pm and actually ended up leaving at 10:45. It kind of felt like flying did a few decades ago. There was tons of space – both leg room and there was no Hunger Games style jostling to snag space in the overhead compartment. We also got served a meal. When we booked, I had specified that we wanted the vegetarian option. I was working on the assumption that it would be gross and full of cheese so I brought lots of food with me. Plus I wasn’t too worried because how much do you need to eat between 11pm and six in the morning, right?

It turned out to be not that bad. It was a curry with lots of vegetables. Quite spicy but surprisingly good. 

We slept-ish. 

And then we arrived 45 minutes early. To a beautiful sunny day. Possibly a bit too bright if it isn’t too outrageous to complain about such a thing. We kind of emerged blinking like hedgehogs. It was still the middle of the night for us.  

Getting through customs looked a bit like it was going to be a gongshow. Our flight arrived at the same time as a whole bunch of other flights and there was a sea of people. There was a guy whose job it was to shout and gesticulate about what line to get into. (The signage trend hasn’t hit Lisbon yet). It was a surprisingly efficient system and we got through quickly.

We had one of those miraculous airport experiences where our bags came spitting up onto the luggage carousel just as we walked up to it. Like they were saying – ‘ah here you are, we’ve been waiting for you.’ This was both good and bad (though way more good). 

Only bad because… in our usual last-minute, let’s create an unnecessary amount of complication and urgency – we decided to get some of those luggage tracking air tags. Of course they were sold out everywhere we looked except at one place in Yorkdale mall. So we battled traffic and mall parking and picked them up for $150. The idea being that you pop these things in your luggage and then you can see exactly where it is through an app on your phone. 

Since we have honed everything we need to live and work into those bags – it seemed like a good idea. 

So it was just a tiny bit anticlimactic to have the bags waiting like old friends at the carousel. But mostly a relief!

As tired as we were – it was a little more difficult than usual to find the secret spot where Ubers are allowed to pick up passengers at the Lisbon airport. (Arrivals level near the Kiss’n Fly – if you ever need to know). Same location as folks use to drop off people when they don’t want to actually park. There is room for about twenty cars BUT about 100 cars looking for spots. It’s like a deadly game of musical chairs. 


We are in Lisbon for 5 days before we go to Madeira for a month. We decided to try something that I’ve been circling around for awhile now. As working remotely and the digital nomad lifestyle is becoming so popular, there’s a growing culture of co-living spaces. 

After a year of going the Airbnb route Rob and I have realized this about ourselves: we can quite easily spend a month happily just talking to each other. It’s one part shyness, one part really enjoying each other’s company and five parts ‘how the hell do you meet people?’

In the last few decades we have met people through kids’ activities, group exercise things like swimming and running, work, being part of stuff in the community… None of those apply to our current lifestyle. How do you filter out all the strangers that cross your path every day for people that may have common interests? In my twenties, when I was backpacking my way around the world, I met other travelers. I’d crack open my Lonely Planet and find a hostel to stay and just naturally start talking to people.

I would also look askance at the occasional strange old person who was trying to blend in to the scene and think – who are they kidding? And when I say old – I mean like 30’s or 40’s. Not nearly as old as Rob and I are in our fifties! 

When we first started looking at some of the digital nomad co-living spaces, it seemed a lot like the hostel experience I remember. Single twenty somethings that could stay awake past ten o’clock. We didn’t want to commit to a whole month of feeling like ducks totally out of water. So our 5 days in Lisbon has been a perfect place to try it out. 

We signed up with an organization called ‘Outsite’ which has a couple of locations in Lisbon. We are staying at the smaller, and I think, quieter of the two. The host was super friendly and helpful even before we arrived – reassuring me that we could show up for an early check-in. Phew – especially considering the transition from roll to drag in the suitcase situation! 

Our Room

It’s a lovely little place. More upscale than the hostels of my younger days. Our room is like a really nice University dorm room. Lots of cupboard space, a comfortable bed, a big desk and even a tiny little balcony. We don’t have a private bathroom. That’s an option but it just wasn’t available when I booked. But it is right across the hall and the other couple that share it are super considerate with timing, smells and cleanliness 🙂 The communal areas include a kitchen, a living room area with couch and TV, a big table with lots of space for people to work and/or eat and quite a spacious walled courtyard with quite a bit of privacy for calls. There’s a huge fridge where each room has a designated shelf. The cupboards are divided by room number as well. Ours is high enough that I need to drag a chair over to access stuff that gets shoved to the back. 

Pretty easy to pick out which shelf is mine…

I think it would drive me a bit batty to have to cook in this kitchen for a whole month. The other folks staying here at the moment are mostly Canadian (which is pretty funny that we have traveled this far to hang out with other Canadians) so we spend a lot of time apologizing to each other in the kitchen. It does mean that I can’t create a disaster as I cook. Plus I wouldn’t be able to film any demo videos or anything. The kitchen and workspace are all together. But having said that – it is nice to be able to easily have all my usuals like oatmeal and green smoothies. 

The grocery store is a few steps away and there are mini-mercatos on every corner selling fruit and veg. 

We are the oldest people staying here but not by as many decades as I had feared. One couple is in their forties and the others are all in their thirties (maybe late twenties). It’s not super party-party. It’s a fun group. Lots of friendly chat and tons of exchange of helpful information on everything from cell phone plans to where to get coffee. 

My surprising and delicious bowl

After we dropped off our stuff that first morning, we went on a mission to find some coffee and breakfast. At the bottom of the hill near our Outsite (everything in Lisbon is either at the bottom or top of a hill) is a cafe straight out of a movie set for ‘European Location’. It’s got cobblestones, little outdoor tables, pigeons, the full ambiance. The coffee is delicious. On that first morning I was prepared to eat whatever there was and figure out the nuances of whole food, plant based when I wasn’t operating from a place of sleep deprivation. Huge pleasant surprise – they had lots of options. I had the most delicious bowl of quinoa and chickpeas and greens and veggies… 

Before we even left for Lisbon we were invited to join the WhatsApp group. So far days leading up to our arrival we were seeing all the invites going out for getting together for dinner and drinks and exploring adventures. And that’s why we were trying this out – so we could meet people. 

When the call went out – ‘Anyone interested in going to dinner at 8 or 9 at Restaurante Cabacas?’ on our second night – Rob and I said that we were. We had an address and we knew we were meeting Connie. And quite a loose arrival time 🙂

We arrived at a few minutes after 8. It took us awhile to figure out that we had arrived because there was no actual sign for the restaurant – just a gaggle of people lined up outside. The side of the restaurant that faced the street was made up of open doors. We didn’t even know if Connie was a man or a woman – and they weren’t responding to WhatsApp to say if they were there or not. At first we tentatively stood near the entrance with the vague plan that we would ask a staff person in our non-existent Portuguese whether one of the tables had someone named Connie. Not a great plan.    

I will confess it was tempting to think – well we tried – now let’s wander off back to our comfort zone and eat on our own…

But decided to go for one more attempt. I started going through the crowd outside asking people whether they were Connie. And we found her! Our group ended up consisting of James, a pilot for Southwest Airlines, Leanne from Israel, Marcus a software engineer fresh off the plane from Boston and Rob and I. (And Connie of course who is also from the US)

Slab ‘o meat hot rock cooking

The restaurant was not one I would have chosen. The menu was a long list of different cuts of meat and fish. You ordered and then each person was given a tray that had an extremely hot rock embedded into it. Then the idea was to slice off a hunk of meat/fish and cook it to your liking. Luckily there were side dishes that you could order which included a (what turned out to be) delicious mushroom dish and a lovely big salad. Rob totally caved and got steak. I had a bite – it was good. 

Here’s an interesting thing to know about Lisbon. When you sit down at a table in a restaurant there are appetizer type dishes already there – things like olives, and cured meats and a bread basket. If you crack into them and start eating – you get charged for them. Luckily, James, the pilot, had traveled quite a bit in Portugal and gave us fair warning. Not that it would have been expensive. For our table of six – all of our food and multiple carafes of wine was only 100 Euros. 

The conversation was so interesting. This is exactly why we decided to go out of our comfort zone. In retrospect we should have called it a night after our long and lovely chatty dinner. That was our instinct but we over-rode it. We were all having so much fun that it only made sense to move onto a wine bar. And then a sangria bar. And then it was 3am and we were stumbling back up our hill… The next morning was not a good time 🙂

Pink Street

So far we’re really enjoying exploring Lisbon. I’m currently at a co-working cafe. Which is a place where you can set up and do hours of work without feeling like you need to keep ordering so much coffee that you will have to go without sleep for 2 weeks. It’s actually really cool. There’s little booths that you can go into to do private calls and video conferences. It’s really nice to just be around other people tapping away at their laptops. 

We are off to Madeira tomorrow. 

So many hills
Time Out Market