The 3 Biggest Travel Mistakes I've Made

Traveling can be one of the most rewarding experiences, but it’s not always the easiest. Flight delays, highway traffic, and crowded destinations are just a few of the issues you could run into when you leave home on an adventure. And unfortunately, if you’re not careful, you can create problems of your own — no outside help required.

I love being able to explore new places, and I feel a huge swell of gratitude when I think back over the trips I’ve taken. I know I’m not the only one — recent data shows that travel spending is up 4.1% through July this year compared to last year.

I’m no pro, but I consider myself a fairly seasoned traveler. However, that hasn’t stopped me from making mistakes over the years that have cost me money and time. Here are three that were particularly painful.

1. I booked the wrong pickup date for a rental car

This year, I was finally able to take a long-delayed trip to Iceland. My husband and I initially booked the trip in February 2020, just a few short weeks before the pandemic lockdowns began. That meant we had three years to research and dream about the trip we’d someday take. But no matter how prepared you think you are for something, life has a way of reminding you that nobody’s perfect.

We took a redeye flight that departed on a Thursday and landed on a Friday. And unfortunately, we booked our car rental to begin on the first day of our trip…Thursday. Oof. We realized our mistake as we boarded our flight and immediately contacted the car rental company. Luckily, the representative told us it wouldn’t be a problem that we missed our pick-up window, and they would hold the car until the next day.

While we didn’t have to scramble for a new car rental at the last minute, we did lose out on the money it cost us to rent a car for a whole day we weren’t even in the country for.

2. I agreed to a timeshare presentation that would not end

This one didn’t feel like a mistake at first, but looking back, it definitely was. On a tropical vacation, we thought it would be worthwhile to sit in on a timeshare tour. The arrangement provided a free breakfast at the resort’s gorgeous ocean-view restaurant, we got to walk the lush grounds, and we’d receive a voucher for a boat tour later in the week.

We confidently entered the presentation, expecting a quick spiel and rapid exit. Hours later, we were still being shown room after room after room in the hotel. My previous confidence in our ability to say “No thank you” and move along was dashed against the brick wall of the guide’s stubborn salesmanship. It was frustrating, and frankly uncomfortable, to face such pushy tactics, and it really soured our day, even after we finally escaped back to the beach.

While I thought I was making a good bet to get a free meal and boat tour, what really happened was we wasted half a day of our short vacation. Here was this lovely trip that we’d planned and saved up for, and while we didn’t lose money in the process, we definitely lost time that could have been much better spent.

I feel like this was a mistake I repeated a lot in my 20s and have since grown out of, but the time it came back to bite me the most was after a two-week solo trip through Ireland and Scotland. I knew I’d have an amazing experience and would want to squeeze as much time as I could out of my PTO, so I booked my return flight to land on a Sunday, expecting to walk back into work Monday sleepy but satisfied. Cue the flight issues.

My plane out of London was delayed and eventually canceled, leaving me teary-eyed and scrambling to find accommodations for the night. All of a sudden, I was out the price of a very expensive last-minute hotel room in London, and I was going to have to borrow an extra day of PTO to make up for the day I’d be missing.

While travel delays are often out of our hands, I’ve now learned to buffer in some extra time as a cushion, just in case. Best-case scenario, I get an extra day or two at home to unwind before I have to get back to work.

Don’t make your trips more expensive than they need to be

None of these mistakes were truly damaging to my personal finances, but I certainly would have preferred to avoid them. There are certain things I do ahead of time to make my trips as affordable as possible. That way, I feel more comfortable absorbing some of these pricey surprises that can pop up as I travel.

For one thing, I always use my travel rewards credit card to pay for my trips. Not only does this earn me points that can offset the cost of my vacations, but many of these cards also offer travel insurance to protect cardholders when things go off the rails.

I also choose to budget for travel ahead of time so I don’t have to borrow money to pay for a trip. This helps me avoid expensive credit card debt that would make a trip cost more than paying for it all upfront.

Traveling the world isn’t the simplest of things, but to me, it’s always worth it. Just make sure you do what you can to avoid any expensive mistakes that can take away some of your enjoyment.

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