A decade’s worth of international travel has shown me how anything that can go will go wrong. While there are plenty of ways to get from point A to point B, I’ve never allowed minor setbacks to get in the way of experiencing a wonderful trip—particularly for a destination proposal! Here are a handful of circumstances thrown our way traveling from the US to the Maldives for the first time and how I outwitted travel constraints.
Adjust to cancellations from inclement weather
We were supposed to go from JFK to IAD via Delta Airlines as the first leg of our trip, but the flight was understandably canceled three times due to a pending snowstorm. Rather than fret and frown, I quickly booked two one-way Amtrak train tickets from Moynihan Train Hall at Penn Station (NYP) to Washington Union Station (WAS), which roughly took the same amount of time. Since train tickets were not as rigid with their seating, we actually snagged a spacious spot in the eating cabin where we had our own table (and more legroom than a traditional airplane seat would anyways) to spread our belongings and enjoy our ticket to ride to the capital.
Form contingencies for award waitlists that do not clear
As I’ve read many times on the AmEx website: “Once you transfer Membership Rewards points to a Partner Loyalty Account, they cannot be transferred back.” Initially, I planned for us to arrive in the Maldives via Qatar Q Suites and depart via Singapore Airlines. Despite tracking availability on Q Suites for months for the specific week I wanted us to travel, the availability never cleared and I ultimately shifted gears to completing a first-class Emirates redemption instead to get to the Maldives. I was able to transfer AmEx points to Singapore Airlines in hopes of getting a business class fare on our trip back to the US, but I could only redeem a waitlisted award. It eventually came to the point where we were still on the waitlist 2 weeks before departure, so the award flight never cleared and I now had 300K points stashed with Singapore Airlines that I needed to eventually use within the 3 years to prevent the points from expiring. Luckily, I found availability on Air France Business Class instead and was able to redeem that through the growing pile of Delta SkyMiles I accrued over the years. The lesson here is to always diversify your points collections for extra cushion in edge cases where waitlists don’t work out in your favor.
Prioritize the plus one in seat selection
When traveling domestically on Delta, I never care to select my seat because nearly most times I get upgraded to comfort or first class. So when traveling with a companion (which adds complexity to the upgrade queue), I sometimes forget to confirm our seating arrangement on the plane. Some airlines do a better job guiding you to confirm seat selection than others. For example, I secured neighboring first-class cabins with Val (EK 232 on Seats 2F and 2K) after redeeming the flight on points. After I purchased our tickets from Air France, a whole week went by with me not confirming our seating details until I received a reminder, and when I went to do so, I noticed that all the middle seat configurations in a 1-2-1 business class cabin were taken. So I reserved the next best configuration with her in 3A and me immediately behind in 3B.
Compartmentalize the essentials for snap packing decisions
Traveling in two separate sets of climates (tundra and tropic) required us to be strategic with what we brought in our carry-on luggage. While we only brought with us two suitcases, we ended up with two more carry-on items (Park Hyatt Panama hats with their own casings), which forced us to check items en route to our Paris destination. We ended up having to check in our luggage at the front desk counter, which meant that we had to hastily fit in whatever we wanted to wear overnight in Paris in our backpacks. I swapped out my Cole Haan boat shoes for my Tim boots and Val also pared down on the essentials. The makeshift adjustment in packing happened in real-time as folks were waiting in line behind us, and time was of the essence in order to catch our flight. It felt like one of those chaotic Amazing Race segments, but I’m glad we both knew how to pack modularly to make the most of every cubic centimeter in our everyday carry.
Screenshots save time when handling health records
I’ve lost track of the number of health declaration forms we had to complete between the US, Maldives, and France. While our wait times in between airport lines were minimal in retrospect, we eventually learned to be more ready to present the generated QR codes through captured screenshots instead of having to scroll through the actual live website (WiFi in airports remained spotty) or present the printed versions of the health declaration forms. Given that we had to produce a negative COVID test to enter and leave our key destinations within variable windows of time (anywhere from 96 to 24 hours in certain scenarios), staying healthy was paramount to our freedom.
Even as a Type A hyper-organized person, all the planning I could have done for the trip could have been sidelined had I not been flexible enough to roll with the punches. I’ve always viewed traveling to unfamiliar countries as an adaptive activity—an adventure not for the faint of heart. Adventurers who use points and miles tend to thrive because they have the appetite to swallow risk and recalibrate resilience when things don’t go as planned.
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