Let’s be clear upfront. Every single member of the 10xTravel team is very fortunate to travel as often as we do and to do so by using miles and points. Without miles and points, much of our travel would not be possible.

That being said, we’ve all made mistakes booking travel or redeeming Ultimate Rewards points for cashback — why Anna, why?! — so we wanted to share some of our learning experiences so you don’t make these same mistakes.

Some of these mistakes aren’t quite as tragic. Rather, we simply didn’t make the best choice for booking some fun business or first-class flight. Woe is me! What I hope you’ll take away from this, though, is that we’re all trying to figure out the best ways to use our points and miles regardless of whether we’re trying to book an economy, business or first-class flight.

In the end, we just want you to have a fantastic time traveling without breaking the bank. The better you use your points, the more trips you’ll be able to take. Now, without further ado, please proceed to judging some of us — especially me — mercilessly.

Spencer Howard

Sometimes, simple really is better.

A few years ago, I started researching Asiana Club. It doesn’t get a lot of chatter because there are only two ways to earn miles. You either earn them directly via its co-branded Bank of America card or you transfer Marriott Bonvoy points. Not exactly the easiest miles to earn.

Since I like to dig into the unknown a bit, I spent waaaay too much time studying this program. In some ways, it was worth it since I learned you could book the Etihad Apartments from New York (JFK) to Abu Dhabi (AUH) — though, that’s not currently an option — for only 80,000 Asiana miles compared to 115,000 American miles or even more Etihad Guest miles.

However, I went a little overboard. I needed a last-minute flight from Europe back to Washington, DC and, as luck would have it, Lufthansa had made some first-class award space available to partner airlines for booking. Knowing that I could use only 50,000 Asiana miles to book, I couldn’t help myself.

So few miles for such an amazing experience including the Lufthansa First Class terminal.

Here’s the thing, though. You can also book this flight for 70,000 Aeroplan miles. Both Asiana Club and Aeroplan pass on the surcharges, so the taxes/fees won’t be cheap either way. The difference lies in how easy they are to earn. Aeroplan is a partner of Amex Membership Rewards — and now Capital One — which makes miles sooooo much easier to earn.

So, yes. I used as few miles as possible but I was too clever by half. I would have been better off booking with Aeroplan. In fact, if you’re thinking about booking Lufthansa first class, Avianca LifeMiles is now a partner of Amex Membership Rewards, Capital One, Citi ThankYou Points and Marriott Bonvoy but doesn’t impose surcharges. Even at a higher rate of 87,000 LifeMiles, you’ll save a ton of cash.

If you take away one thing from my experience, don’t forget to consider how easy or difficult it is to earn the miles and points necessary to book your trips. It’s not just about the redemption rate.

Anya Kartashova

One of my cringeworthy redemptions was back in 2012. I was booking a weekend trip to New York City and had accumulated a bunch of Delta SkyMiles by using the Delta SkyMiles® Gold American Express Card for my everyday purchases (add that one to the list of regrets).

My ticket cost $430, but instead of redeeming 25,000 SkyMiles plus $11.20 for a round-trip ticket—Delta award charts still existed back then—I ended up using the Pay with Miles “perk” of the credit card and paid 30,000 SkyMiles plus $130 to cover the rest of the fare.

Pay with Miles is a feature available to Amex Delta card members for flights operated by Delta. It makes it possible to apply SkyMiles at a rate of 1 cent apiece toward any cash ticket available on the website.

Delta Airline

The worst part is that it wasn’t the only time I used this redemption method for a Delta flight. I was an inexperienced rewards collector, and I didn’t know all the ins and outs of the program.

The good news is, I know better now. The bad news is, Delta has eliminated award charts and booking award flights with SkyMiles has become a game of crapshoots and ladders. You never know the mood Delta is in, and any flight can cost you upwards of a million miles.

Believe it or not, this still haunts me. I’d redeemed at least 50,000 Delta SkyMiles this way, and I just can’t even! Who was I?

John Tunningley

Similar to Anya’s story, when I first started out using points, I wasn’t exactly sure what I was doing. I was super excited to be getting some free travel and not worried about the value I received from the points.

The most horrific thing I ever did was redeem my Freedom points for cashback before realizing I could transfer those points. I’ve mentioned that before and that doesn’t make much of a story and it makes me cringe to think about the fact that I received at least $300 in cash, meaning at least 30,000 Ultimate Rewards went to waste.

But when it comes to travel redemptions, the one I look back on and most regret is using 37,500 American airlines points to book a domestic round trip to LAX with the return flight in first class.

Looking back, I lucked out and had found some saver award availability and likely got around 2 cents per point in value but at the time I didn’t know a thing about first-class products, airline alliances, or even seating arrangements. I ended up spending one leg of the flight in a simple increased legroom seat and the other half in a middle-of-the-road domestic first-class seat.

Without realizing what international business and first-class products looked like, I thought I was really living the high life but if I could have those points back I would take them back in a heartbeat. I consider myself quite fortunate and, without any children, I’m at a point in my life where my schedule is pretty flexible and (thanks to points and miles) can take 2-3 international trips a year.

Personally, I value American AAdvantage miles incredibly high since they can book top tier products like Qatar Airways Qsuites and Etihad Apartments, so those miles could have done so much for me today.

In the end, I was relatively happy with the trip and redemption at the time but I also recently had to purchase a few American Airlines miles to top off my account for a big redemption. Maybe I’m just living in the moment but I hate having to purchase miles (it’s usually a terrible value) so I wish I could have those miles I spent years ago back in my account today.

Anna Zaks

I redeemed my Chase Freedom points for cash for years before I found out about the Chase Sapphire Preferred® Card and the ability to transfer the points to travel partners. Like many, I was skeptical and didn’t believe that travel rewards can amount to much. Little did I know! My husband and I always used credit cards for everyday spend to earn points (re. cashback).

I wish we learned about this wonderful world of travel rewards years earlier.

Unfortunately, this is a very common mistake. I’ve had many people tell me they cash out Ultimate Rewards points earned on the Freedom or Chase Ink Business credit cards. Ultimate Rewards points are so valuable when used as travel rewards points, so please don’t be like me and don’t cash them out.

Now that I know better, I always keep at least one premium (i.e. card with an annual fee) Ultimate Rewards earning card per family. Paying an annual fee is worth it for the ability to transfer points to travel partners or booking travel through the Chase travel portal. I’ve booked so many great non-chain hotels through the portal! I’ve also booked quite a few international business class tickets when I transferred the points to United Airlines.

United Airlines

I am glad I took the time to learn about the transfer partners, airline alliances and partnerships and now can really maximize the value of my Ultimate Rewards. I’ll never cash them out again!

Matt Brown

Editor’s Note: Matt wins the award for the world’s smallest violin.

It was in the middle of February 2018. We were getting ready to embark on our 3-week long trip to Australia, which was going to be our first big trip where we flew roundtrip in international business class. I was wrapping up some trip logistics and details and I thought – why the heck didn’t you book at least one of the legs in First Class, not just Business Class?

We booked these flights in March 2017, as soon as the award booking window for our desired travel dates opened. There was wide availability on our desired flights from New York (JFK) to Sydney (SYD) with a connection at Seoul Incheon (ICN) in all classes of service – economy (40k United miles one-way), business (80k United miles one-way), and first-class (120k United miles one-way).

I had picked this somewhat indirect routing through Seoul on Asiana for a few reasons:

1) the opportunity to fly on an A380 for the first time,
2) I wanted to fly round-trip in at least business class, and
3) United is finicky and unreliable with offering saver business class seats on their flights.

I’d always heard that the service and detail on Asian carriers was top-notch so I wanted a chance to experience it.

We ended up booking our round-trip flights in business class for 320,000 United miles (if booking again, I’d consider using Avianca Lifemiles instead). Even though I was sitting on a healthy and plentiful stash of roughly 700,000 Chase Ultimate Rewards points at the time, it pained me to spend that many miles on one trip. I was only about 18 months or so into learning about points and miles, and was definitely still in the hoarding phase where I wanted to earn earn earn, yet struggled to actually redeem them for anything other than saver economy seats.

So fast forward back to February 2018 again right before our trip – at this point, I was regretting my decision not to book at least one direction of our trip in first class. I had read a few reviews of Asiana first class and had a serious case of FOMO.

In the hopes of last-minute availability opening up in which I could correct my mistake, I regularly checked award space in the last 3-4 weeks before our flight to see if any first-class space had opened up on our outbound flight. I was ready to fork over an additional 80,000 miles + the approximately $100 or so I thought it would cost to make the change if spaced opened up… but it never did.

So, while our travel from the US to Australia was superbly comfortable, with endless amounts of champagne, and complete with the high level of attention and service that the Asian carriers are known for, there was definitely a bit of FOMO wondering how the people in those 12 incredible first-class suites at the front of the lower deck were enjoying their flight just a little bit better than I was. All because I was being a little bit cheap and didn’t want to fork over extra miles.

To make it worse, in the spring of 2019, Asiana announced that they will no longer sell first-class seats on any flights starting September 1, 2019, so I’ll never be able to get to experience it. So you can bet I won’t make this mistake again, and have my eyes set on booking a first-class award on airlines such as Cathay Pacific, Korean Air, Japan Airlines, and ANA on my radar to make up for this. We just have to decide on a destination, and then we’ll be riding shotgun for sure this time.

Joe Cheung

This may be recency bias, but the redemption I’d do differently is the recent Delta Vacations deal. While everything worked out in the end, the deal ended up causing me quite a bit of stress – and I only have myself to blame. Mostly.

When the deal first hit, I decided to pass. Even when news started coming out that the deal was allowing people to redeem Skymiles for 2 cents per point – even towards things like Disney World tickets which are notoriously hard to get deals on – I resisted letting FOMO get the best of me. So, I let a full two weeks of the promo pass as I blissfully relaxed and planned other trips.

The day before the promo ended, I saw a tweet from Doctor of Credit about how someone on Reddit tried to game the promo to make Disney vacations even more lucrative. Against my better judgment, I decided to finally start going down the rabbit hole to see if Delta Vacations could help save me money on my Disney vacation.

After hours of tinkering and maximizing, I had an itinerary (including tickets) that I was happy with. At this point, it was 1:30 AM and there were less than 24 hours left in the promo. I got to the very end of the booking page and agreed to use my 59,000 Skymiles for the reservation. I got a “loading” symbol for a minute or two and then an error: please try again later. Thinking my internet was a little wonky, I tried two more times in the next ten minutes or so. Same error.

It was late, so I decided it was time for bed. But right before I left my computer, I noticed something to my horror – Delta had taken 59,000 Skymiles from my account. Three times! So at 2:00 AM I made a call to Delta vacations, who weren’t able to fix the problem immediately.

Long story short, I got my reservation done and got the 118,000 “extra” miles that had been deducted back. But I had put myself through way more stress than necessary. In the end, I would do this differently based on these lessons:

1 – Nothing good comes from procrastinating on a deal. Make up your mind quickly and jump on it or move on
2 – Nothing good happens after 2 AM
3 – Always remember to factor in the time you might lose fixing a deal gone wrong

Like I said above, my situation was totally avoidable and I only have myself to blame. I’ll be sure to book or get off the pot next time!

Julie Szpira

In June 2019, I traveled to Spain with a friend.  Correction, I traveled to Spain with a very trusting friend. I booked her a one-way ticket to Spain with the promise, “I will get you home in time for your company meeting.” I know it sounds crazy to book trips to different continents without having a way to get home. However, when you have a variety of points and miles, you have many options.

We booked our flights to Spain in October 2018, and at that time, the options for flights home weren’t great. I decided we would wait to book until better availability or routings opened up.

After spending a couple of fabulous days in Madrid and an even more fabulous couple of days at the Park Hyatt Mallorca (one of Bryce’s new favorite hotels), my friend began to get antsy.

Park Hyatt Mallorca

I buckled down and found award space on Star Alliance carriers. The flight would transport my friend from Palma de Mallorca (PMI) to Frankfurt (FRA) on Lufthansa and Frankfurt to Washington Dulles (IAD) on United.

United Airlines offers a one-way economy fare from Europe to the United States for 30,000 MileagePlus miles, plus associated taxes and fees. The airport and passenger taxes were around $60 for the itinerary. There would also be a $75 close in booking fee. In total, I was looking at 30,000 miles and $135 dollars for a transatlantic flight booked 3 days before departure. I was pretty pleased with myself.

Since I’m always striving to find a great redemption, I wanted to see if I could do better. Singapore Airlines offered the same itinerary for 27,500 miles. At $85, the standard taxes and fees booking through Singapore Airlines were slightly higher than on United, but Singapore Airlines does not charge that pesky close-in booking fee.

I would be transferring Chase Ultimate Rewards to United or Singapore, it seemed like a no-brainer to choose the option that required less points and less cash.

Well, this is where my redemption went wrong. Points transferred from Chase Ultimate Rewards to Singapore Airlines are not instant. I transferred my miles and then spent the next 24 hours refreshing my Singapore Airlines app, hoping that the points would appear in my account so I could book her ticket.

Once the miles were in my account, I realized I had to designate my friend as a Redemption Group Nominee before I could use my miles to purchase a ticket for her.  That process wasn’t too hard, but it was a step I wouldn’t have had to take with United.

The nail in the coffin for this bad redemption was that I couldn’t book a ticket online. I had to call Singapore Airlines and book over the phone. Since I was traveling internationally, I didn’t have my normal phone access. I had to use my Skype account to make the call and then position myself just right to keep the WiFi signal strong enough to remain connected.

After about 45 minutes of getting disconnected multiple times and having Singapore Airlines call back, the reservation was completed.

I was victorious. I had saved $50 and 2,500 points. Instead of feeling accomplished, I felt stressed and aggravated. Sure, I booked a cheaper ticket, but if I could do it all over again I would have spent more and just booked on United.

Travis Cormier

When traveling on points and miles, flexibility is key. Sometimes, being too flexible can make a trip a bit difficult.

On my recent trip to the Maldives, this flexibility really got to me. It doesn’t matter how nice they are, spending hours on end in an airport lounge isn’t ideal – although it does beat paying $20 for airport Burger King.

On my way to the Maldives, I had a 10-hour layover in New York and a 10-hour layover in Hong Kong. On the return, I had an 8-hour layover in Sri Lanka.

I had lounge access on each layover, including access to some pretty stellar lounges — the American Airlines Flagship First Dining lounge in New York and Cathay Pacific first class lounge in Hong Kong were amazing. I won’t say the same for the SriLankan Airlines lounge in Colombo, but it still beats sitting at the gate.

It was a fairly complex booking that necessitated the flexibility, but I don’t think I would do it again. Even in the nicest of lounges, you can only take advantage of the amenities so much. Plus, I lost over an entire day of travel spent in lounges.

You’re probably wondering why I didn’t get out and explore the cities. Well, I had just finished working a night shift before heading to New York – and I don’t sleep well on flights without lie-flat seats (spoiled, I know). I was exhausted and in no mood to be out in busy New York City.

In Hong Kong, I was skipping the final segment of a paid ticket and didn’t want to risk being questioned upon return. In Colombo, it was a redeye layover, and the airport isn’t conveniently located for sightseeing.

Rather than spending so much time in lounges in order to take more business class flights, I probably would have sucked it up and flown economy on some of the shorter flights, such as the Male to Hong Kong flight instead of routing through Colombo. This would maximize the time I had at my destination, and reduce my time spent in lounges.

Don’t get me wrong, I love lounges. But 3-4 hours is more than enough time to really enjoy the amenities offered. I’d rather spend my time at my destination than watching movies in a lounge just waiting for my next flight.

Caroline Lupini

This might sound a bit crazy, but the one redemption I would have done differently is that I wouldn’t have flown the Etihad Apartments.

The Etihad Apartments is one of the most sought after experiences in the sky, and it was only the second time I had redeemed miles for a premium cabin because I had heard about how amazing it was. And don’t get me wrong, it absolutely was a stunning experience.

But, here’s the problem. I was supposed to be finishing a tour in Iran, so I had to fly home from there. But then, due to visa complications at the last minute, I wasn’t able to go on the trip at all. I was able to call American Airlines and get my award ticket changed, without a fee, or so I thought. But when I arrived at the airport in Doha to fly the rest of my itinerary home I ran into issues because the ticket wasn’t reissued properly. Ultimately, the issue was fixed after about four hours on the phone. But that’s still not the whole reason why I would have done this redemption differently.

You see, once I finally got my boarding passes in Doha, I still had to fly from Doha to Abu Dhabi to New York to Washington DC to Detroit. It was a long day, and by the end I was exhausted and a little bit crabby (though the start to the day sure didn’t help with that either).

I could have spent less miles and taken a more direct itinerary from Doha to Chicago to Detroit with Qatar Airways in Business Class. It still would have been very nice and I would have saved a few thousand miles for my next redemption.

The lesson I took away from this experience is to not chase aspirational redemptions too hard. Sometimes taking the more direct route is the best option.

Photo Credit: Qatar Airways

Final Thoughts

If you feel like slapping Matt, Travis or me after that, I don’t blame you. But, seriously, I hope we’ve shed a little light on the different speed bumps you can face on your journey with miles and points. Sometimes, it’s as simple as not realizing how to extract value out of your points and miles when you first start — we’ve all been there.

Even the more experienced of us makes mistakes or make suboptimal decisions. It’s all a learning experience. The hurdles you face as a beginner versus when you’re experienced might be different but it’s still important to learn.

At the beginning, you really are just trying to figure out what’s going on and it’s easy to miss better opportunities. As you learn more, the challenge then becomes not overthinking or being too clever when a simple solution will work.

In the end, we’re all grateful for the chance to travel and we’ll keep learning from our mistakes.

What is a redemption you wish you could do over again? How would you do it now?