Booked: A Careful COVID Colombian Caper

It’s always a pleasure to write from the sky. In this case, that means it’s official: I’m off to Colombia for three weeks for my first major international trip of the post-COVID era!

I’ve been quite cautious to travel since the pandemic began, content (though hardly satisfied) to be patient and kind to myself while I’ve focused on other priorities at home. Now, it’s time. Full stop.

Here’s a breakdown of what I plan to do, and how I came to the decision to travel here, now, and in this way.

My Itinerary

With so many compelling attractions and a desire to move at a sensible pace, the trip has quickly ballooned to a rich three-week itinerary, with a mix of accommodations and activities.

First, I’ll be landing in the capital city of Bogotá. I’ll be at the Artisan DC Hotel, an Autograph Collection property, for two nights.

I’ll then hop over to the W Bogotá for one night, where I’m embracing my Titanium Elite benefits in style, using a Free Night Award worth 40,000 points and a Suite Night Award to confirm the best available free upgrade.

Then, I’ll move onto Medellín for five nights, where I’m staying at the Marriott. Medellín in particular is known as an up-and-coming digital nomad hotspot.

I’d wager that most visitors consider it to be Colombia’s most compelling cultural destination, both for the country’s violent history and vibrant present. It was an easy choice to spend the bulk of my time.

Next, I’ll be in the mountainous coffee plantation town of Salento for three nights. There, I’ll unplug from the bustle of the city. I’m looking forward to getting some light work done in tranquillity while tapping into Colombia’s natural landscapes.

After that, I’m off to the coast for the rest of the trip. The first stop is the four-day Lost City Trek – think hipster Machu Picchu.

I’ll be bookending the multi-night hike in Santa Marta, as I typically do to prepare for and recover from a wilderness expedition. I’ve got a single night before and after the hike booked at the beach-adjacent AC Hotel in town.

I’ll then take a few days as a beach bum to relax. I haven’t picked my exact destination yet, but I’m quite open to slumming it at a hostel (with good Wi-Fi, of course). From there, I’ll take a day trip to the magnificent Tayrona National Park.

Finally, I’ll wrap things up in Cartagena as I ease back onto the grid at the Ermita, a Tribute Portfolio property. I look forward to exploring the old town and squeezing in some extra beach time.

Getting To, From, and Around Colombia

For the outbound journey, I’m flying from Vancouver to Bogotá with a connection in Toronto. Searching about six weeks out, I found award space for 48,300 Aeroplan points + $78.14 in taxes and fees in business class.

I made sure to book routes with Signature Class service on both flights, to get the most value out of my ticket.

By flying Air Canada metal on both legs, not only did I avoid the $39 fee for travelling on a partner airline, but I also saved points. With no partner on the ticket, the price band is calculated based on the great circle distance between the origin and destination, not the total miles flown.

This is a huge benefit for those of us on the West Coast, where we often have to make a circuitous connection to reach South America. Indeed for this route, it’s the difference between the two Aeroplan pricing bands.

I also saved points as an American Express Aeroplan Reserve cardholder and Aeroplan 35K member, with preferred pricing bringing the points cost below the lower bound of the published range of 50,000 points.

Coming home, I’ll be departing Cartagena on Copa Airlines, connecting briefly in Panama City and Cancun before catching the Air Canada Dreamliner to Vancouver.

I booked this for 50,000 Aeroplan points + $132.20. Despite the partner booking fee, it was the most direct route home that fit with my schedule, with friendly dynamic pricing for the Air Canada leg.

Within Colombia, I’m using Avianca cash fares to travel between Bogotá, Medellín, Salento, and Santa Marta. The country is quite large and mountainous, making road travel prohibitively slow.

Last-minute domestic cash fares can be had for as low as $10 (or more with a checked bag). I’d say that’s a no-brainer given the substantial time savings over taking a bus. Plus, I’m happy to get the quality of service I’d expect from a global airline, but at low-cost carrier prices.

Along the coast, I’ll stick to road transport as I explore smaller towns. I’ll finish with a five-hour bus ride from the Santa Marta area to Cartagena, where there is no direct flight between the two.

COVID-19 Travel Considerations

I’d always been eyeing Winter 2022 as a personal target to resume international travel. Indeed, the precautions I’ve taken for my own health are as good as possible, the social responsibility of not spreading the virus is under control, and societies are reopening to the point where I’d be able to enjoy my destinations for what they offer.

My speculative bookings became a comedy of errors. Heading to Beijing for the Olympics got scrapped as foreign spectators were unwelcome. As for Emirates First Class to South Africa Omicron ground zero, need I say more?

With high case numbers in Europe, heavy travel restrictions in Asia, and the general challenge of Africa, I turned my attention southward. Both the viral transmission rates and the testing requirements looked much friendlier in the Americas.

The pandemic-related barriers to Colombia are, at this point, non-existent. Armed with our trusty COVID-19 travel resource, I’d been tracking a few potential destinations, and it’s quite clear that Colombia is following Canada’s Omicron curve, with a quick rip and dip, but at half the height.

It would be no more risky to go out for a meal or a drink at home than in Colombia, or to go through the airport process, both of which I’ve been doing comfortably the past year. Also, vaccination rates are as close as I’d expect to Canada’s for a less developed country.

Furthermore, the only impediment to public life is a mask mandate, the same as at home, and which for me is actually reassuring given that we’re not out of the woods just yet.

Additionally, Colombia has no testing requirement or quarantine for fully-vaccinated travellers. With Canada moving to rapid antigen tests by the time I return home, any remaining hassle has been dispelled, and it became easy to commit.

I’ve shifted from a mentality of “wait for things to get better” to “strike while the iron is hot” with respect to the ebbs and flows of COVID-19. While I believe the world is firmly trending in the right direction, I have no qualms about globetrotting somewhere I deem safe as soon as things are looking good, in case the opportunity passes me by.

The Right Trip at the Right Time

As someone with a wide range of travel styles and goals, I often find it hard to choose from an endless sea of possibilities. When you want to see the entire world, how do you even begin to decide where to go next?

The global pandemic has only made it harder for me, with meaningful travel such a far-off concept for so long. I’ve struggled with what travel means to me, and with my sense of who I am as a traveler.

When choosing my next adventures, I try to be in touch with my own travel needs. I like to align my internal state with my external destination as best I can, and let the delightful unknowns work themselves out from there.

Colombia had been high on my list for many years, although I’d never prioritized it. It rose to the top at this moment in my life for a handful of reasons, not just for pandemic-related factors.

What has stood out to me most from the time I’ve spent backpacking in Mexico, is that I felt like the people I met were drawn to the same destinations as me, for the same reasons. We were on the same wavelength in ways that I haven’t felt in other parts of the world, and I think that says a lot about the destination itself.

It’s a sign that I’m in the right place at the right time, and for that reason, I’ve long been keen to visit other parts of Latin America.

I plan on doing a mix of sightseeing, remote work, and relaxation, which is a travel style I’ve been eager to try, but hadn’t ever had the opportunity. That balance seems to be a strength of Colombia’s, further cementing my desire to visit.

Of course, the climate in February is a huge plus. I’d call it the high side of shoulder season, after the holiday rush but before the wet season. Mountains and beaches alike will be very pleasant.

Finally, Colombia seemed like the right balance between accessible and challenging, as we re-emerge into the world. It’s so bizarre to go to a new continent as a “practice trip” – but here we are.


I never expected my first trip to South America, a budget-friendly continent, to be powered by Miles & Points. But I think that surprising outcome is a testament to the many changes in our lives, both as a society and for me personally, over the past two years.

I’ve long been curious to try short-term remote work without going fully adrift as a digital nomad. I’m at a point in my lifestyle and career where that isn’t just possible, it’s part of the job!

As I get older, I’m also appreciating the value of nicer and more private accommodations. It gives more control over the travel experience. While I’m all for the unexpected, and I’m hardly opposed to the less glamorous options, I need a bit of predictability and comfort if I’m going to juggle work and play in tandem.

On that note, I’m curious to embrace some new ways of connecting with other like-minded travellers in the absence of a hostel environment. I’m interested to see who I connect with, now at a much different place in life than the last time I went on an adventure like this.

I’m keen to check out some cafes or co-working spaces as I come to appreciate cities around the world as more than just tourist destinations, but as rich societies that I can not only view from afar, but also tap into and feel for myself.

I’m filled with excitement at the prospect of relearning how to travel. The growth that we get by stepping out of our comfort zones hasn’t been widely available, at least not in this way, for far too long.

I can’t wait to see what Colombia has in store for me as I kick off my next chapter of travel.

  1. Mak YYZ

    I just came back from this beautiful country Josh. took advantage of cash fare on avianca for $400 YY-BOG RT, then internal flight of BOG-CTG-MDE-BOG are for $50. Under $500 visited 3 cities from toronto and spend 10 days in total.
    Beautiful city, nice weather and great food. Used Fourpoint sheraton for 5 nights (50k bonvoy) in MDE, Hampton inn hilton in CTG for 20k which is the worst property..could have gone to Hilton but 50k per night felt not worth it as both of them are pretty much on the beach.
    Bogota used Tequindama Suites for $60CAD instead of marriott or hilton due to their kitchen and spacious 1 bedroom suite with sofa bed.
    Will have to retun again to explore the interior places like the santha martha and other mountain/coffee plantation places.
    Have fun.

  2. johnny lu

    How are you finding these 10$ Avianca last-minute domestic cash fares?

  3. Jaime

    You’re going to my home town Santa Marta. You’ll love it!!

    1. John

      Santa Marta was nice to visit. It has almost as many hi-lites as Cartagena.

  4. Rich

    That’s a great itinerary. Enjoy Colombia, it’s a special place. Good luck on the hike to la Ciudad perdida.

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