My Trip Cancellations that Actually Worked Out for the Best

I don’t know about you, but I am a bit obsessive when it comes to trip planning. I do tons of research and truly put my heart into the process. I’ve long said that miles and points hobby attracts OCD types, so I have a feeling many of you can relate. It’s not good or bad, it’s just the way it is.

So when I read Frequent Miler post written by Nick on how he had to scrap his amazing family trip to Fiji at the last minute due to son’s illness, I honestly felt sick to my stomach. Obviously, in the grand scheme of things, it’s not a major tragedy, but still. I can only imagine how many hours went into planning this beast of a trip, and for all of it to fall apart must really hurt. Kudos to Nick for (mostly) recovering financially from this disaster.

Last year I almost had to cancel my family reunion in Europe because so many things went wrong right before the flight, including my daughter’s illness. I still can’t believe the trip was a go because it felt like the universe was conspiring against me on that one. But the truth is, the more people you have in your travel party, the bigger chance there is of something going wrong. And the risk goes up exponentially when you have little kids.

Missing my brother-in-law’s wedding due to baby’s stomach bug (but first flying all the way to Pennsylvania)

So, it’s important to plan a trip and hope for the best, yet prepare for the worst. With many programs eliminating re-deposit penalties, using miles has become far more attractive than it was in the past. Yet, most folks will still have some nonrefundable expenses, especially when it comes to international trips. Using the right credit card can certainly help, but it won’t always protect you. I’ve just paid $1,100 for an old machiya rental in Kyoto, and it will become nonrefundable two weeks before our trip. And a lot can happen in two weeks!

So, it looks like I need to purchase a policy via insuremytrip.com I was going to just get a medical coverage plan and rely on my Hyatt credit card for the rest (see related post). But I honestly don’t know if it will cover a vacation rental. Plus, the comprehensive travel insurance plan only costs $13 more and has primary medical coverage. It also covers mileage redeposit fees, something no credit card offers. So, despite the nuisance of filing my recent travel insurance claim, I think I will go with a standalone option after all. I’ve always being of the opinion that it’s better to over- than under-insure. Especially if you are a person of limited means.

But more than anything else, it’s good to keep a positive outlook. Even if you end up canceling a trip, sometimes things work out for the best. Here are a few examples from my own life.

Finding the silver lining

Back in 2019 I booked a Costa Rica anniversary getaway for me and my husband. I was so looking forward to it, but the trip had to get scrapped due to approaching hurricane. This is the problem with scheduling travel from/to Florida in the fall months, yet I keep on doing it for some reason. Anyway, I was extremely disappointed, but what can you do. We ended up going with my in-laws to a Florida state park and spending a night in a simple cabin (after having a few mishaps along the way).

After that we visited Cedar Key, a neat island where my FIL used to land his Cessna airplane.

Due to Covid pandemic we had to put off our trip to Costa Rica, but we finally made it there in 2022. Talk about perfect timing. We ended up getting upgraded for free to Nayara Tented Camp (their newest wing that wasn’t even built in 2019). Waiting a few years, though not by choice, was the best thing that could have happened. An absolutely stunning resort if you can swing it financially.

Private pool fed by natural springs

But the biggest silver lining to staying in Florida in 2019 was the fact that we were able to spend time with my FIL who passed away only a few months later. Even if we never made it to Costa Rica, I would still say that cancellation was a blessing in disguise. It allowed us to make more memories with my FIL, something you can’t put a price on.

I feel the same way about canceling a stay in Baker’s Cay Key Largo Hilton resort at the end of 2019. My FIL ended up in the hospital a few days before we were supposed to drive there for winter break. At the time he was in stable condition, and my husband said we should go ahead and keep our plans since the kids were really looking forward to a stay at this resort.

My FIL has been in and out of the hospitals quite a bit by that point, and somehow always pulled through. But not this time. I’m so glad I insisted on canceling the trip. It allowed my husband to spend many precious hours with his dad before he passed away.

We did eventually make it to Baker’s Cay at the end of 2021 and actually snagged a rate of 42k points per room instead of 60k points I paid in 2019. See my review. That was a temporary fluke due to Covid pandemic, as the resort now costs 90k points per night. Things rarely work out that way, and almost never with Hilton points. But miracles do happen.

Unfortunately, sometimes a trip is canceled and you never get a chance at a redo due to worsening health. That’s why I’m not a fan of waiting until your circumstances are 100% perfect when it comes to money, etc. But in majority of cases, a cancellation is just a temporary setback. Thanks to miles and points, it’s relatively easy to recreate the same itinerary in the future. Yes, usually it will cost more, but not always.

I’ve had to cancel our trip to Japan three times now due to Covid pandemic, but I’m pretty stubborn and keep on rebooking. Plus, due to recession in Japan, right now everything there costs 25% less than it did in 2020. So, I’m hoping to file that one under “silver lining” as well…if we don’t end up canceling.