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.
- Another good sweet spot here is 50,000 Singapore Airlines miles (transferrable from all major currencies) for business class tickets from Africa to South America.
- 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 Kayak.com, 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.
Do-Over
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.
Refunds
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!
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Thanks for sharing. But who are you and where did Jeremy and Winnie go? Lol
Witness protection program and some extensive plastic surgery later… lol
Fair question! Jeremy has been publishing my posts on his blog for nearly two years now (first post here!), but they have mostly been focused on the nuts and bolts of award travel. He let me branch out a bit and so I occasionally write award-travel-adjacent things like this, which are not meant to replace his content but to add some practical context to utilizing points and miles. Thanks for reading and sorry for the scare :)
Edit: realized my bio at the bottom wasn’t showing when the article was published. Oops!
Gosh, one day I hope to be as good as you with points. I always feel like I’m not maximizing my usage. Great post!
The only poor redemption is the one you don’t make! Keep learning and practicing and you will figure out the best ways to use points in a way that works best for you (which doesn’t mean you need to book a trip to the Maldives like many points blogs preach!).
That’s not extremely nice calling people from Santiago, Chile short and cheap.
I have a friend from Santiago and while not particularly tall, she is quite free spending. 😉
LOL – how rude of me! I have been to Santiago once before and very much enjoyed it. A thousand apologies!
Hi Brandon!
Nicely written article. I do believe you dodged a pretty big bullet by not getting to go to South Africa! Are you in Panama City now? I’ve been here with my husband since Jan. 15, until April. Lots to do/see here, but very HOT and humid, especially all afternoon. We had hoped to spend 6 months in Mexico but it seemed safer in Costa Rica/Panama so here we are. Have fun, if you are out and about and would like to meet up or would like some tips/pointers, I’d be happy to help.
Hey Jeanne! We dodged a bullet with SA indeed; it wasn’t a week after we canceled our flights that we began to hear of Omicron and we definitely would have been caught out given our schedule. Still bummed to miss out on the trip (and the flight in CX F), but better to play it safe.
My question exactly. Last I heard Jeremy and Winnie bought a house in California. You look like nice people, but it would be great if you could introduce yourself. Your story sounds very interesting. Thanks!
Sorry for the bait and switch, Erik! I’ve been writing for Jeremy for almost two years (first article) and my bio is at the bottom of the article, though I am happy to tell you more if you have questions. I mostly write about award travel but thought it might help explain the concepts a bit better with a practical example. These days I spend just as much time reworking travel as I do booking it!
Edit: realized my bio at the bottom wasn’t showing when the article was published. Oops!
Take the challenge and flip it to opportunity. Well done.
During the depths of the pandemic, I went deep into the Rocky Mountains–rather than going abroad (impossible). I saw parts of the country I would never have seen otherwise.
Cheers!
If anyone knows how to pivot, it’s you! Going abroad is great and usually preferred, but sometimes you just need to work with what you have and not force it.
I get concerned about transfering points to airlines other than the big US ones (.e.g., Delta, AA, United, SW). I worry if I cancel flights the points will be stranded somewhere I can’t easily use. Do you worry about that?
Yes, that can be a concern. For example, I now have over 100k points with Avianca which is a bit more obscure than United even though you can book Star Alliance flights with them. I’m confident I will use them eventually, the trick is keeping them from expiring until then! If there were ever a case when I was very unsure about being able to use the points if a trip got canceled, I would think twice about that redemption – sometimes it’s worth paying a little extra for the confidence, especially during a pandemic.
go brandon
Go Ken!
Wow. Sounds like a lot of work, exacerbated by a pandemic. Happy to hear it worked out for you. We have been traveling through Mexico for almost seven months now. Flew back to the states once and then back to Mexico using miles. Most of our travel through Mexico has been through their great and affordable buses. Going to head to Asia eventually. However, we just received another 180 days in Mexico and have some flexibility as a result. Not sure we will stay the full 180, but it’s nice to have that option in our back pocket.
It’s a labor of love usually, but can certainly be difficult to unwind a complicated trip. We love Mexico and are planning tp spend a lot of time there in the coming years!
Really enjoyed Guadalajara – heartily recommend. Great weather and fantastic food.
Thanks for the recommendation! We haven’t been to Guadalajara but to several cities nearby and like the area a lot.
I get that you’ve used points for flights, but what about the months of nights? Points for stays or paying out of pocket for nights? That adds up quickly. Years ago, when programs were still generous, we did several month long around the world trips paid for with points on both flights and nights. Sadly, those days are long gone.
We do a mix of hotels and AirBnBs. When staying at hotels, we try and save up our points for luxury places we wouldn’t normally pay out of pocket for as opposed to a lower-end place for more nights. For AirBnBs we can occasionally get gift cards at a discount or as given to us a gifts, but mostly we just book small, affordable places with the amenities we want and it usually ends up being far less than we would pay for a rental in the U.S.
Gotcha, thanks.
Jeremy, please add a way to get a reply or new comments emailed to us. You’d get a lot more website traffic, plus we can come back when someone replies to our comment. WordPress makes email subscribing easy.
OK, done
We have done much the same as Brandon although we do generally go for more nights vs super luxury places with points… not much opportunity for enjoying luxury stays with 2 kids at the moment.
I generally have a $/pt target and use the hotel points if it comes out ahead financially. It also helps to use things like the 5th night free with Marriott or pick Airbnbs with discounts if booked weekly, etc…
In 6 months or so in mexico, turkey, italy and the balkans we did much the same. Have no interest in luxury places and find that hotel points are better used in the US where hotels have become very expensive.
airbnb and mid and low grade hotels were a bargain even in northern italy vs california or arizona. In mexico city there are very nice midgrade hotels for mid 20s to 30 a night.
I’m interested in this type of travel, so I found your story interesting, both as to the original trip and the revisions. My question is, what do you do with your home base during long term travel? We are considering selling and putting stuff into storage, or maybe just downsizing. Leaving a house unoccupied for long periods makes me uncomfortable, but also having no real home to come back to feels pretty uncomfortable also! What do you do for this?
We don’t have one single home base, per see, rather we have 4 properties in Maine that we rent out short-term or seasonally throughout the year. When we’re back in Maine we live in one of them and rent the others, then rent all of them while we travel. It takes some work to maintain, but that way we don’t have a house just sitting there.
More specific to your question, though, is that in the house we usually stay in we partitioned the basement into an area for guest use and a locked storage area for our stuff while we’re away.
Look into house sitting or house swaps.