São Miguel, Azores, Portugal

After all these years and after becoming conversational in Portuguese, somehow I’ve never been to Portugal, a pretty popular place in its own right. It’s right next to Spain, too. So… Let me just skip right over it (insert meme song here) and fly to the middle of the Atlantic Ocean instead. Sounds logical, right?

Well, the Azores are still Portugal. Maybe not the first thing that comes to mind though, since they’re an autonomous region. Even some of the mainland Portuguese visitors I encountered slipped up and called it “going abroad.”

I’ve been fascinated by these little dots on the map ever since I saw the largest city, Ponta Delgada, had relatively short direct flights from Boston, home to a large Azorean diaspora. Though I never took the opportunity to go while I lived in Boston, they’ve stuck in my mind ever since. Why are these little isolated islands so inhabited? How’d they become part of Portugal?
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 Empordà / Girona, Catalonia, Spain

It’s funny how fast and intense travel friendships can be. Usually it ends with people extending an open invitation to visit their homes: hey, I’ve been on both ends of that. As genuine as they are, more often than not, these invitations are aspirational, seldom followed up.

It’s thus all the more surprising which friendships endure. I spent barely a day and a half with Gemma and Ramon in Sri Lanka seven years ago! We pulled a memorably freezing all-nighter, hiking up those 5500 steps, before parting ways in opposite directions with each other’s recommendations. Occasional messages over the years gave way an increasingly serious desire on my part to act on their open invitation to visit. And so here I am!
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 Barcelona, Catalonia, Spain

It’s rare for me to visit a place twice. Even when it comes to visiting friends, it takes me ages. Without friends though, it practically never happens. There’s one big thing different this time that brings me here.

En route to visit my friends Gemma and Ramon deeper in Catalonia, timing led me to make an impromptu weeklong stay in Barcelona, just in time for the biggest cultural festival of the year. (Shoutout to Rob for telling me about it, and sorry the timing didn’t work out for Valencia!) They set me up with their friends in Barcelona, Mar and Ignasi, who could not be more welcoming and hosted me despite a week where were all too busy to actually hang out beyond a dinner or two. It’s still enough to form another fast friendship, and I hope we find an opportunity to pick things up again just as I’ve been doing with others on this trip.

While waiting for the main attraction on the weekend, before and after my weekday remote work hours, I spent a whole lot of time aimlessly walking around Barcelona. It’s nice for once to not have any pressure to see the sights or do touristy things, to relax at home whenever I felt like without feeling a loss of time, and to have a mix of old and new.
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Where do I even begin? 10 years is a long time. How do I even start a conversation? “Hey! It’s nice to see you! Long time no see! How is everything?”

10 years is enough for the world to visibly change. From the last time I’ve been here, we’ve gone from paper maps, big cameras, and day-ahead bus ticket purchases at the booths to the ubiquitous, always-connected smartphone. From the last time I’ve really talked to these friends, we’ve gone from Facebook to Instagram to an opaque, increasingly toxic algorithm pushing away any sort of personal content and whittling away already-tenuous connections literally separated by oceans. It’s made keeping up even on a circumstantial level more difficult, and time has worn the initiative it takes to keep in touch.

From the last time I saw these friends, many now have children. I’ve only ever known them while travelling, and now our lives have taken very different directions. And for the most part, I admit I haven’t really been great at keeping in touch either. So it’s with a bit of trepidation that I proposed this trip — am I imposing on them, am I being a burden? Am I merely a reminder of a past life? Aside from the good times we’ve shared, what drew us to become friends in the first place, and do we continue to share anything in common 10 years later? It’s with immense gratitude and a little bit of surprise that I’ve been so welcomed with open arms.
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Galápagos Islands, Ecuador

Immediately upon arrival in Puerto Ayora, the largest town in the Galápagos, I spent two hours inquiring at every single agency down the main thoroughfare. I beat my previous time, found a reasonable price and a desirable itinerary, played hardball and negotiated a better deal, and I did it all entirely in Spanish. Allow me to toot my own horn here, cause I’m a little proud of myself!

What previous time? Well, the three hours I spent in Ushuaia arranging a last-minute cruise to Antarctica 10 years ago. This time, it’s a last-minute cruise around the Galápagos, a place I would have loved to visit 10 years ago but didn’t have the budget for, naturally, after that rather large expenditure.

So. While I wait for departure, what now? After all, in the Galápagos, it’s all about seeing the animals here, and that can seem somewhat inaccessible.
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Cartagena and San Basilio de Palenque, Colombia

There’s a whole lot to unpack in Cartagena. If you’re coming from the bus terminal, nearly one hour away from the city centre, you’ll pass through what most locals probably see: sprawl, traffic, markets, and your average non-descript Caribbean living situation. Honestly, parts of it reminded me of Guyana.

If you’re coming from the airport like I was (because bussing from MedellĂ­n would’ve taken 15 hours), you’ll see affluent suburbs. Follow the road and hug the coastline, and you’ll end up in Bocagrande, a neighbourhood of ritzy hotels (and only hotels) and some city beaches along a narrow peninsula. Seen from afar, you might be reminded of Miami like I was.

If you take a boat tour or come from a cruise, you’ll probably have visited or passed by the white-sand beaches and turquoise waters, with the downside of crowds and touts trying to rip you off for a beach chair, umbrella, drinks, and food. That too sounds a little familiar.

Those are all options though. What everyone comes to Cartagena for are the city walls, the colourful houses and balconies, the sense of being transported to another place… and another time.
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Medellín and Guatapé, Colombia

MedellĂ­n is everyone’s favourite story. Long notorious for drug cartels and violence, the city was deemed the most dangerous in the world in the late 80s and early 90s. Now, it’s made a remarkable turnaround in security and reputation, and is better known as a world vanguard of urban planning innovations, the cultural capital of the country, and one of the buzziest places in Latin America. Locals love the place, they’re friendly, and they’re proud of its progress. Foreigners flock here in droves, enticed by the backstory, the nightlife, the creature comforts, and the luxury for cheap.

In theory, this is a place that I too should love. I can see why so many people do.
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 Salento and Valle de Cocora, Colombia

What better way to meet up with a friend for the first time in six years than to arrive in town in the middle of the night, both of us having taken night buses from different cities and unable to sleep from going up and down twisty mountain roads? It’s in a hostel dormitory in Salento where I reunited with Mathieu, a friend with whom I’ve had a storied travel history since 2012. Always a pleasure… Maybe except when we’re both sleep deprived and incoherent.

We didn’t plan to be in Colombia at the same time, but found some overlap in our itineraries. Mat, having lived and worked in Colombia for a year a while back, is on a greatest-hits nostalgia tour of sorts. Of course, that’s gotta involve one of the most scenic and (especially recently) rightly popular regions in the country: the Zona Cafetera. At least that’s why I’m here.

But first, a nap.
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Bogotá, Colombia

Ten years ago, when this blog began, I ended my northwards trip of South America at the equator. What’s past the equator? Colombia. The rest of this trip is addressing unfinished business. While I’m not resuming from where I left off by land, it’s gratifying to be able to celebrate a milestone, reflect on my last ten years and how far they’ve taken me, and also simply to keep a promise I made to myself to return.

Travel itself has changed since ten years ago as well. Not so many travellers I met back then on the gringo trail were visiting Colombia, then a destination with only nascent buzz after its years of instability lent it a reputation of dubious safety. Nowadays, it feels like the whole world has caught on. Everybody is here. Hostels are full, walking tour groups are everywhere, and tourists of all ages and abilities flood the Candelaria, the historic old town and touristic center of Bogotá. Colombia’s in its moment.
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Jarabacoa and Bayahibe, Dominican Republic

I’ll be honest and say up front that I never really had the Dominican Republic on my radar before. I mean, what do you think of when you think of the DR? All-inclusive resorts, sure. (Flying from Ottawa to Saskatchewan via Punta Cana, definitely.) Baseball? Reggaeton and loud blaring music? Adventure tourism? I can appreciate all of that (except for the satire-friendly political grift), but I wouldn’t include any of those things amongst my preferences.

But hey, when in Rome DR…. I’m here for the wedding of my dear friends Paul and Louise, along with a small group of our friends who’ve all flown in from Vancouver. While I’m not staying with them in the resort, this event did bring me to the country, and I chose to explore a little with the few days I had before it.

After Santo Domingo though, I was definitely looking for a little bit of respite from the hustle and bustle. Mountains, fresh air, and quiet? Sounds great. Oh look, Santo Domingo weekenders!
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