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6 travel hacking tips I learned the hard way

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It’s been said that one way you get good at something is to fail enough times at it that you learn from your mistakes. Here are six lessons I have learned about miles and points and am now sharing in the hopes of preventing you from having to learn them the hard way like I did.

Reward travel is not free

Social media posts like those starring an influencer living it up in a lie-flat airplane seat sipping champagne while bragging about how the flight was “free” are guaranteed to make my blood boil. Travel with miles and points will always have a cost associated with it, no matter how points are redeemed. 

Award tickets can have taxes and fees upward of a thousand dollars per ticket. You’re going to have to pay for transportation to and from the airport—and unless you plan on eating every single meal in a hotel or airport lounge you’re on the hook for meals. Oh, and unless your idea of a pleasurable trip involves doing literally nothing, you’ll be paying for activities (although you can actually use points for some activities too). 

And that doesn’t even begin to tally the hundreds or even over a thousand dollars that many miles and points collectors pay in credit card annual fees.

A normal travel card portfolio could consist of a premium travel card for airport lounge access, a mid-level travel card that earns points in a flexible program, one mid-level airline card for free checked bags and one mid-level hotel card for status benefits. Those four cards alone could run you almost a thousand dollars a year in annual fees. I’ll confess to paying multiples of this for my own card collection. 

When I first started, I used to think of award travel as free until a friend asked me a very good question: “What could you have earned if you had used a cash-back card on the same spending?”

She had a point. Even if you pay all of your expenses with earned rewards and pay no annual fees, award travel still has an opportunity cost—the rewards you could have earned with a cash-back card. You’re giving up your cash rewards when you redeem for travel. I’m not saying traveling on rewards isn’t worth it, because it can help you see places you otherwise would have only dreamed of.

But to say that travel using miles and points is entirely “free” is simply a lie. 

Points are not an asset 

You do not own your points, the loyalty program does. This means that any program can devalue what their points are worth without telling you. There was even a hearing recently with the Consumer Financial Protection Bureau (CFPB) and U.S. Department of Transportation about this topic.

Hoarding your points is generally a bad idea because there is no guarantee of their future worth. It’s all about earn and burn. 

I have been burned more than once by devaluations, most recently by Delta. I am sitting on about 250,000 Delta miles that I am having trouble spending, even with the TAKEOFF15 benefit (providing a 15% discount when booking award travel on Delta flights using miles) I have with the Delta SkyMiles® Platinum American Express Card.

Just this month an economy flight to Madrid priced out at 85,000 SkyMiles after the discount. The exact same flight priced out at 15,000 miles using Flying Blue.

Advice is helpful, but FOMO is dangerous

Once you get a taste of how miles and points can transform your travel, it’s easy to fall down the rabbit hole of travel rewards content on social media. And once you do, it’s equally easy to see a dozen of the aforementioned business class airline redemptions and assume there’s something wrong with you if you fly coach. There isn’t. The back of the plane arrives at the same time as the front. 

You’ll also see influencers bragging about staying in rooms that are worth thousands of dollars a night on points, enjoying marble bathrooms the size of your apartment and one-million thread count bedsheets. There’s a hotel—The Park Hyatt Vendome in Paris—that was so overhyped for a while that I started to call ostentatious consumption for the sake of it “Vendoming.” 

I’m not saying I don’t redeem miles for business class, but I can say that I don’t do it every time. And I’m not saying I don’t love five-star hotels, but if it’s a trip where I’m only sleeping in the hotel room, it’s not worth spending extra points that I could use for another trip.

I deleted Instagram for a long while precisely because I found myself making decisions that looked great—on someone else. I only got back to social media when I had a firm grasp of what made sense for me. Don’t let fear of missing out make you burn points in a way that aren’t worth it for your life. Travel in the way that makes sense for you and your goals.

Hotel points can be hard for families to use overseas

I can’t tell you how many parents I have encountered who have diligently collected hotel points but are disappointed when they realize that once you leave the U.S. they’re pretty much impossible to use if you need more than two people in a room (unless you are willing to get two rooms).

There’s a reason for this: Occupancy limits and fire codes are much more firmly enforced overseas than in the U.S. and I’ve even seen even 1,000+ square-foot suites that technically don’t sleep a family of four.

I absolutely do not recommend trying to skirt these rules. I know people who have successfully done so, but also know people who have been marched out of hotels for trying to squeeze extra people into a hotel room.

So on our big trips, I usually only use hotel points for the airport transit hotels in-between stops. In fact, on a six-week family trip to South America I used hotel points for a total of two nights: one for the airport Holiday Inn in Santiago, Chile and one for the airport Holiday Inn in Buenos Aires, Argentina. 

The good news is that many hotel chains, including Marriott and Hyatt, have branched into vacation rentals. The cents-per-point value is not optimal, but isn’t horrible, and this may be your only workaround for overseas trips with kids using hotel points.

In general, if you know you’ll be using vacation rentals you’ll be much better off collecting flexible points like Capital One Miles that you can redeem toward travel or even earning on a cash back instead.  

Capital One Venture X Rewards Credit Card

Intro bonus


Earn 75,000 bonus miles after spending $4,000 on purchases within the first 3 months from account opening






Annual Fee $395
Purchase APR 19.99%–29.99% variable
Foreign Transaction Fee None


Airport lounges are overcrowded and many aren’t worth visiting

As someone who has had airport lounge membership via a credit card for over 20 years, I’ve noticed that lounge access has become a victim of its own success. It’s not at all uncommon to arrive at a lounge to find a line outside and a hostess taking names as if you were at IHOP on a Sunday morning. 

And I’ve visited some lounges that made me wish I were at an IHOP. At least at IHOP your food is freshly prepared and generally palatable, which isn’t guaranteed at many lounges. Platters of Ritz crackers accompanied by day-glo cheese product and a ginormous tin of crusty penne alla vodka were front and center at more than one lounge buffet I’ve spotted in the last year. 

Now there are some lounges I will set aside time for—Capital One Lounges spring to mind—but in general I’ll just arrive closer to departure and head straight to the gate. 

Monthly and annual credits from credit cards are meant to go to waste

(Looking at you, Amex.) 

I’m currently wearing a Fitbit Versa 2 watch. It’s nice, but an Apple Watch would have made more sense for me.

But since I had an The Business Platinum Card® from American Express card that I was about to cancel, I needed to spend the $200 credit for Dell purchases that cardholders get every six months. And I frankly have so many chargers, converters, and earbuds collected from Dell over the years that I ran out of things to use the credit on. And, for six years in a row my husband got popcorn from Saks Fifth Avenue for Christmas thanks to the personal The Platinum Card® from American Express, which I have since canceled (IFKYK). 

I live and breathe credit cards so I have a spreadsheet tracking my credit card credits, but unless I order both Uber Eats and Grubhub every last day of the month even I don’t redeem them all in time. 

The dirty little secret: Credits are set up this way on purpose. The vast quantity of unused benefits is called “breakage” and it’s baked into the profit margin. That’s why the Hilton Honors American Express Aspire Card card’s hotel credit is split in half-year increments and is good only at resorts, which comprise less than 5% of Hilton’s portfolio. And don’t even get me started on credits that are broken up quarterly or monthly.

The takeaway

I’ve been able to take some amazing trips with my family using miles and points. We’ve seen fireworks explode over the Eiffel Tower on Bastille Day, watched the Macy’s Thanksgiving Parade up close and have made so many memories for which I am eternally grateful.

That travel didn’t come without a cost both in money and time. But the journey has been so worth it. So whether you’re ready for that trip of a lifetime or you just want to get away for the weekend, miles and points can help you get there, even if you make some mistakes along the way. 

Welcome to What’s in Dia’s wallet. In this monthly column I’ll share what’s, yes, in my wallet but also what’s on my mind. After over a decade covering credit cards, traveling an average of 100 nights a year, and earning and spending over a million points each year to do it, I’ve learned a few things. If you have questions or ideas for future topics please reach out to me at creditcards@fortune.com. Dia Adams, Senior Editor


Fortune Recommends™ has partnered with CardRatings for our coverage of credit card products. Fortune Recommends™ and CardRatings may receive a commission from card issuers.

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