Travel Hacking Mistakes WE Still Make

In life, there’s always room for improvement, that’s for sure. And that holds true for the travel hacking world that each of us creates. Talking about mistakes we make is never an easy conversation, but Grant and I had it anyway. Whether the mistakes are the once-and-we’ll-never-do-that-again type, or those reoccurring mistakes that we seem to make over and over again, shedding light on the mistakes helps us think through what we’re doing and perhaps more importantly, what those mistakes might be costing us in the way of miles and points. After admitting our mistakes and deciding to share them with you, Grant and I had a good laugh about it all. Then he went back to enjoying his chai latte and I finished off my cortado, and of course we vowed to wipe the slate clean and not make the same mistakes again.

Let’s Take a Look at Our Mistakes

Grant felt that maybe searching and booking award flights and hotels too far out is a mistake because there are often good deals if you wait to the very last minute.

I think, though, that this speaks to one’s travel style. I think maybe Grant is mixing apples and oranges. For example, for award flights, are you talking long haul flights or Southwest short flights? And are you locked in to certain travel dates or do you have maximum flexibility? Also, how many are traveling? Some good deals with award flights open last minute, though it surely depends on class of service and the other particulars of your itinerary.

As for booking hotels too far out and thinking this might be a mistake, if good deals appear you can always book at a lower rate. Also, I think once people book a hotel, they don’t give it to a site like Pruvo or don’t ever check the prices again. I think that’s a mistake. I always check on my Citi Prestige reservations and if the prices go down, I call the Citi Prestige team and they get the lower price. I did this recently with one of my Asia hotel stays where the price went down. The price on a hotel I have booked in Europe went down, too. That was sweet!

The next travel hacking mistake Grant brought up was that he pays for premium economy/economy comfort seats when you can sometimes snag those seats for free when you check in 24 hours in advance. Again, it’s assuring you have what you want versus taking the chance it “might” be available later on. Grant said he’s more willing to risk it if he’s flying solo and less willing to take a risk if he’s flying with someone else. This makes sense.

The third mistake Grant mentioned was keeping credit cards that have annual fees for too long and expecting that he will get enough value out of the credit card benefits to justify the annual fee. This is a good one, and a mistake perhaps we all make. When Grant mentioned this, I realized I have to handle this mistake, too. I need to create a system for checking and assessing the value I get from each card. Some are obvious and some are less so, but going forward, I need to do some thinking and make some decisions, so I was glad Grant brought this up.

For me, I think my biggest mistake is that I don’t pay attention to AMEX Offers. That’s leaving miles, points, and cash back on the table. I do look at the emails I get telling me what offers I have, but I don’t go out of my way to check my American Express account. I’ve never gotten into the AMEX Offers habit and I know that’s been a mistake, so I have to get better at it. I promise!

Then Grant and I talked about some mistakes travel hackers make and wondered if we were making them too.

Do we maximize Amazon purchases by buying Amazon gift cards and getting 5X Ultimate Reward Points at office supply stores? I always do. Grant said not always, but he wishes he did.

Do we think to use cash back portals when we shop online? Grant always use Ebates, unless they do not have a store he shops at. I check sites like CashBackMonitor or Evreward to see where the best rewards are found.

A lot of travel hackers ALWAYS use points instead of weighing them against cash. Grant prefers to use points whenever possible, unless the cash price is a better deal. I’m meticulous about checking the points vs. cash value. Even though cash might not be the best deal, if it’s good enough and I have a reason to use those points elsewhere to maximize their value, I’ll still opt for cash. So in the case of points vs. cash you also have to think ahead some and see what your plans are for those points.

Grant still does a lot of app-o-ramas. I think these should be done keeping in mind what you’ll actually use the points/miles for. I asked Grant if he was thinking ahead or if he just wants to grab what he can. Those app-o-ramas can be addictive :) He goes for miles and points that he knows how to use, even if he doesn’t have an immediate use in mind. I wait for certain cards and incentives to appear and haven’t done big batch applications in years, so we’re different on philosophy here.

One mistake I don’t make anymore is about lounge use at airports. I don’t think people realize you can use a lounge when you arrive at an airport before you go to baggage claim or leave the terminal. For instance, when I get into San Diego, especially after a long flight, I go to the lounge on my way to baggage claim. I freshen up, grab a bottle of water, maybe some food and some coffee. If my ride is late, it’s a good place to wait. Grant mentioned that if he has time, he’ll do this, too (stopping at the Centurion Lounge in SFO if he is flying back on United or stopping at the Escape Lounge in OAK, if he is flying back not on Southwest Airlines).

So that’s what we came up with in the way of our travel hacking mistakes. I’m quite sure we forgot a few :) What is your number one mistake? And which ones do you no longer make? Share your mistake fixing tips so we all can benefit!

2 thoughts on “Travel Hacking Mistakes WE Still Make

  1. tina

    Clearly from my experience you can not always get into lounged upon ending your trip. I tried entering (SFO) Centurion on a return trip from Spain last year and they asked for my boarding pass. When I showed them the one I had from the trip I just flew they said no and wouldn’t let me in.

    1. Shelli Post author

      HI Tina, Sorry to hear that. Grant uses the Centurion at SFO regularly and hasn’t mentioned any issues. Hopefully your next Centurion experience will go more smoothly. Thanks for reading and taking the time to reply.


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