As the summer of 2021 was wrapping up, more and more countries began opening their borders to international travelers. Having been hopeful of this, I booked us on an extravagant multi-month round-the-world trip for minimal out-of-pocket cost using award miles and points, only to have the trip crumble and slip through my fingers as COVID-19 flareups and the eventual Omicron variant came into play.

We still managed to get out of the country for the winter, but we ended up in an entirely different hemisphere.

Since leaving our jobs in the Fall of 2020, we have been living in Maine in the spring, summer, and fall and traveling to warmer climates in the winter. We spent the entirety of last winter in Mexico, where my wife’s family is from, and this year we had our sights set on going abroad once again. Here was our tentative itinerary:

  • Fly from Boston to Johannesburg with a month-long stopover in Hong Kong, during which we would take a separate flight to/from Taipei, Taiwan (12,000 British Airways Avios round trip).
    • The BOS-HKG-JNB flight was booked in First Class on Cathay Pacific for just 70,000 Alaska Airlines miles. This is one of the best sweet spots around because they allow for a stopover on a one-way award ticket, plus the sheer amount of mileage covered from Boston to South Africa is insane.
  • Stay in South Africa for about 2 months, then fly to Buenos Aires, Argentina.
  • Visit Buenos Aires for a couple of weeks, then get a cheap flight from Buenos Aires to Santiago, Chile
    • Pay with cash, flights are short and cheap.
  • Travel around Chile for a month or so, then fly back to Boston.
    • Booked in business class for 60,000 Avianca miles, which was really only 48,000 miles because Citi had a 25% transfer bonus.

All told we had paid 180,000 points/miles and about $250 in taxes and fees (each) for a 5-month trip around the world in first/business class. It took me weeks to arrange the schedule, transfer points, and get everything aligned just-so to ensure it would go off without a hitch.

Hanging out with penguins in Cape Town on our last visit to South Africa. We were eager to go back!

Trouble Ensues

A couple of months before we were set to leave, Taiwan announced that they would be closing their borders through the end of the year and tourists would not be allowed to enter. Shucks. I scrambled to look for alternate locations and flights to fill the gap, but at the time almost all of Asia was completely shut down. What’s more, there was no award availability at an earlier date for us to simply go to Johannesburg ahead of schedule (a blessing in disguise, it seems).

I racked my brain for several days trying to find alternatives, but in the end I just couldn’t get it to fit. With so many places locking down, we turned to the Travel Restrictions map on, a wonderful resource for up-to-date travel restrictions, to see what our options were. What we discovered was that there were only five countries with no travel restrictions, and they were all in the Americas and Caribbean.

The Americas and Carribean are the most viable options for American travelers as of December 2021.

On Kayak’s map, green indicates there are no restrictions at all, whereas red means that non-residents are not allowed in. Orange means there is some kind of restriction, but it might only be that a PCR test is required for unvaccinated travelers while nothing is required for those that are vaccinated. Since both my wife and I are vaccinated and have received boosters, we had many more options here than in Asia.


With this knowledge and some experience in Latin America, it was easy to transition our winter plans to an alternative schedule. Here’s what we settled on:

  • Fly to Costa Rica in November, stay for about a month.
  • Fly to Ecuador and stay about a month, including a one-week visit to the Galapagos Islands
  • Fly to Panama, visit for a week or so.
  • Fly to Mexico, stay for 2-3 months and visit areas we missed last year
  • Fly back to New England in April

We put this itinerary together quickly and were able to get some decent deals on flights. For the flight to Costa Rica, we flew Southwest Airlines from Chicago where we were visiting my wife’s family. The fare was only a couple hundred bucks (paid for with our Uber Eats money) and got us positioned nicely in Central America. We then used United miles to book flights from San Jose, Costa Rica to Quito, Ecuador, to the Galapagos, and then on to Panama City for 33,750 miles plus $147 in fees (each) using their “Excursionist Perk” for a free segment. We haven’t yet booked flights to Mexico and back to the U.S., but we’ll likely do so with Avianca miles or cash rates if they are low enough.

Hanging out with these guys in Costa Rica isn’t so bad.

We also have friends and former colleagues in all of the aforementioned countries, which make things easier since they have better knowledge of the changing COVID situation on the ground.


Since COVID-19 started, many airlines have loosened their restrictions on changing and canceling flights, so I was able to get all of our points and miles refunded from the Asia/Africa/South America itinerary for no cost with the exception of the flights from Johannesburg to Buenos Aires. For some reason Singapore Air is being a pain about this and has told me that my cancellation reason (not being able to get into the country) “did not qualify for free cancellation under COVID-19”. I haven’t checked with them since Omicron started and maybe they have changed their tune, but at the end of the day they charge just $75 per person to re-deposit miles so it wouldn’t be a huge loss if I had to do that, though I would rather not pay if I don’t have to.

Now, though, I have hundreds of thousands of miles in programs like Avianca that I have no immediate use for which is generally bad practice because they are then subject to expiration and I might be tempted to shoehorn them into a trip when they aren’t the best value just to use them up or keep them active.

Final Thoughts

The purpose of this article is not to complain about my travel sorrows or make any kind of statement about COVID-19 travel, but rather to show what is possible and what so often happens when trying to book travel to specific areas using a particular airline’s miles or points. Especially nowadays, adaptability is key when planning extensive trips and by having transferable award currencies we were able to completely overhaul a five-month trip without losing our minds. Stay flexible, my friends!

Brandon Chase is a financially independent writer, endurance athlete, and travel hacking enthusiast originally from Maine. He is a former Foreign Service Officer with the U.S. Department of State and spent nearly a decade overseas serving at embassies in Cairo, Egypt, and Nicosia, Cyprus, and Islamabad, Pakistan. Since getting hooked on “the hobby” in 2013, he and his wife have accumulated and redeemed millions of points and miles for luxury travel, including a $35,000 trip around the world for 97% off retail which he wrote about on his blog Fit For Miles. In addition to travel, he loves to be outdoors and has summited Mt. Kilimanjaro, thru-hiked the Appalachian Trail, and completed ultramarathons at the 50k, 50-mile, and 100-mile distances. Brandon is thrilled to share his knowledge of credit cards, award travel, and optimization with the Go Curry Cracker readers and hopes to help people travel more and better than they ever thought possible.

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