How I fixed a rookie travel mistake that nearly cost me $4,000

Quick summary

A travel journalist recounts a major planning mistake involving the International Date Line, which disrupted a complex, multi-country trip.
The error led to a mismatch between flight arrival and hotel reservations, nearly causing significant financial loss and logistical headaches.
Award flight availability was extremely limited, forcing creative use of points and miles across different loyalty programs and travel portals.
Ultimately, flexible points and a travel portal redemption option helped salvage the trip, though not without added stress and partial out-of-pocket costs.

What to consider

Crossing the International Date Line can shift arrival dates, potentially impacting hotel and transfer bookings.
Award seat availability may be scarce on short notice, especially for premium cabins or specific routes.
Travelers should familiarize themselves with transfer partners, travel insurance benefits and tools for monitoring flight changes.

What you'll miss from the article

A detailed walkthrough of how to troubleshoot booking errors using points, miles and award search tools when plans go awry.

Generated by AI with support from our editorial team.

I've been a travel journalist for over a decade, and I'm here to let you know that even we pros make rookie mistakes.

In fact, at the end of the summer, I made such an elementary-level travel error that it derailed a trip I spent months planning — and nearly cost me thousands of dollars to fix. Luckily, points and miles came in and saved the day, and I'm telling my tale as part of TPG's weekly reader mistake series to help make sure you don't make the same simple error.

What happened

My sin? When I booked a flight from Dallas to Fiji, I forgot that I was crossing the International Date Line.

Here's the short of it: For over a year, I was planning a whirlwind trip to Australia with my mom. After months of tracking flights I could book with points and miles across a range of programs, I stumbled on 80,000-mile tickets from Dallas to Sydney via Fiji in Fiji Airways' swanky new business-class product through American Airlines. After mulling it over, we decided that instead of just connecting, we'd extend our layover and spend three days exploring a beautiful country we hadn't visited. Better yet, we booked three nights at the super popular Likuliku Lagoon Resort.

On the Friday before our Thursday night flight, after sitting down to write out an itinerary for my mom (a ride-or-die who gladly goes with me blindly), it hit me: Yes, we leave Thursday ... but our plane lands on Saturday. ON SATURDAY. But therein lies the problem: the hotel reservation, along with our complicated, pre-booked boat transfers, starts on Friday.

My initial thought was just to see if we could extend the stay by one night on the back end of our reservation, but this was no ordinary trip. It was a nearly month-long journey to Fiji, New Zealand, Australia and Hong Kong. There was no way to add a day without causing a domino effect of other changes. The only options were to lose a night in paradise or figure out how to leave the States a day early.

I tried to see if Fiji Airways could move us up a day on their end. No luck. Then I tried American Airlines, which told me I'd have to cancel the award tickets and rebook. (I knew both of us these were long shots, but I had to try.)

But then I ran into the real problem: With less than a week to spare, award availability was practically nonexistent, according to Seats.aero, the award-flight aggregator I turn to first when booking flights.

The day we needed to leave had just one ticket to Fiji available to book with miles, and rather than flying out of Dallas Fort Worth International Airport (DFW), it left from San Francisco International Airport (SFO). That business-class ticket was still just 80,000 miles. "Okay," I thought, "I'll put mom in the front and I'll take an economy ticket." The economy ticket, though, was 100,000 AAdvantage miles. "Hell no," I said. "I'm not paying more to sit in the back of the plane." Either way, I knew we weren't taking the original flight from Dallas, so I canceled the ticket, got my miles refunded instantly and rebooked my mom on the flight from SFO.

Fiji Airways A350 business class — BEN SMITHSON/THE POINTS GUY

That weekend, I tried every trick in the playbook: searching various award partners I could transfer points from my Chase Sapphire Reserve® (see rates and fees) or American Express Platinum Card® to for a different flight, pricing out cash options and, most of all, praying that another award seat would open up. Once again, no luck.

My last-ditch effort was to potentially use my Chase Ultimate Rewards or American Express Membership Rewards to pay myself back for the business-class seat I'd already booked for my mom. Knowing that the cash fare was over $4,000, I went in with little hope. But on the Chase Travel℠ portal, my luck took a turn when I saw that the flight I needed was marked as eligible for the newish Chase Points Boost, which let me redeem my points at 2 cents per point.

I didn't have enough points to cover the entire flight, but the 158,540 Chase Ultimate Rewards I did have, valued at 2 cents each, covered $3,170.80 of the $4,066.50 flight. I paid $895.70 for the rest of the flight with cash. Right now, TPG values Chase Ultimate Rewards points at 2.05 cents each, so I'd say it worked out pretty nicely.

Sure, I probably could have used those points for a better redemption with better planning and more flexibility, but I was in a bind. More importantly, I didn't care about the trips I could take; I wanted to be sipping Champagne with my mom in the front of the plane as we kicked off our wild journey together.

How to avoid this

As long as you're a traveler, mistakes will happen, and things will go wrong (even if it's not your fault). When those things do happen — whether it's a delayed or canceled flight, or you simply write down a date wrong — have a plan of action ready, along with resources like The Points Guy that can guide you.

Download tools like the Flighty app, which often lets me know about a flight delay before the airline does, and Seats.aero, to quickly see what award flights are available I could switch to. Study up on the travel insurance benefits that come with your credit cards, and make a mental note of what transfer partners you have access to.

Most importantly, know your limits. I could have easily just accepted the more expensive economy ticket, but I was willing to give it a few days to explore all of my options. But by the end of the second day, I was burnt out and ready to throw in the towel. Luckily, the Chase Travel portal saved the day, but it was truly my last-ditch idea.

Bottom line

For what it's worth, three nights at Likuliku and exploring Fiji's Mamanuca Islands were more than worth all the stress. This trip wouldn't have even been possible without points and miles. That's the beauty of it: points and miles can be a nightmare and a blessing, a gift and a curse, the means to end and the end itself. Or in my case, all of the above.

Now, if I could just learn to use a calendar...

Want to share your story with other TPG readers? Fill out our mistake story form or success story form. (For ongoing issues that you feel owed compensation for circumstances beyond your control, please contact TPG's ombudsman, Michelle Couch-Friedman, at ombudsman@thepointsguy.com.)

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