Travel Tips

My Initial Experience in the Overwhelming World of Travel Hacking

by Kyle BurbankMay 22, 2024

Over the past few years, my wife and I have had the good fortune of getting to enjoy an increasing amount of travel. This includes heading to domestic locations such as Los Angeles for the D23 Expo and Orlando to visiting Walt Disney World, as well as international travels to Paris, Hong Kong, and Tokyo. Heck, we even went to cities that don’t have Disney Parks, such as when we headed to Washington D.C. to attend FinCon or Las Vegas for various Vegas things!

Despite spending more time away from home, I had always resisted the notion of “travel hacking” with credit cards as I didn’t think I was a frequent enough traveler or big enough spender to get much benefit from such techniques. However, I dipped my toe into the world of award travel along the way — leading to both excitement and a feeling of being overwhelmed.

So what got me to change my tune on travel hacking and how far down the rabbit hole will I go? Let’s take a look at what I’ve learned so far and where I’m learning from.

What changed?

I’ve previously said that travel hacking and credit card churning just weren’t for me. In my defense, I’m still hesitant to try the latter — however I have recently found myself becoming more interested in award travel. That’s partially because I’ve come to appreciate the comforts and conveniences that come with airline status and class upgrades.

Don’t get me wrong — I’ve always been happy to endure what we had to in order to fit a great trip into our budget. At the same time, who doesn’t want to upgrade their experience? Thus, I figured it couldn’t hurt to attempt racking up points while being careful not to spend extra just for the privilege.

Funny enough, during his keynote at FinCon 2019, Ramit Sethi asked the audience what they loved to spend money on. With that answer locked in, he then asked what we would do if we could 10x that spending. This got me thinking that, while I’m certainly not in a place to actually multiply our travel spending by 10 fold, we could still get a taste of that life by attempting to bank points and spend them on a truly special trip — while staying at our favorite “aparthotels” and settling for economy in the meantime.

What is travel hacking?

The basic idea behind travel hacking (as I understand it) is to leverage credit card miles, loyalty points, and more to earn free travel and accommodations. That may sound straightforward enough but, as I’ve learned more, it’s kind of amazing how much can go into achieving this goal. Beyond just earning miles on a credit card or even applying for multiple cards to score sign-up bonuses, there’s also an art in how to use said miles and points. For example, I’ve discovered that you can sometimes transfer points to one airline offering a bonus with the intention of actually booking segments on a different airline in the same alliance as a way to maximize your point value. Seriously, it’s all pretty mind-blowing stuff.

As you can tell, I’m a true novice at this and I’m sure some seasoned travelers are screaming at their monitors while reading this. But hey — everyone has to start somewhere.

My first steps

Every travel hacker needs their first real travel credit card, right? Well, for a long time, I’d resisted the idea of paying an annual fee for a card. But, if I wanted to get serious about earning travel rewards, this would be a near-requirement (although there are some beginner cards with either low or no annual fees).

If you’ve spent any time around credit card forums then you surely know the fervor people have for the Chase Saphire Reserve card. Nevertheless, after doing my research, I actually went with another (and, yes, more expensive) card: the American Express Platinum card. Let me be clear when I say that I did not take this card’s then-$550 fee — now $695 fee — lightly. In fact, I was pretty much in agony while deciding if I really wanted to try it. But, thanks to such perks as airline lounge access, airline credits (as limited as they may be), Uber credits, and more, it seemed to make the most sense for us.

Of course, ever since I applied for, received, and started using the card, I’ve continued to do research on how this whole points game works. Thankfully I’ve found some great resources to help me learn the ways.

The resources I’m consuming

One of my first stops while researching different card options was The Points Guy. You’ve probably heard of this site and there’s good reason for that as, from what I can tell, they’re one of the most trusted and popular travel hacking sites on the web. They not only helped me decide on the Amex Platinum but were also where I first learned of some changes that came to the card later on.

If there’s any knock on TPG, though, it’s that that can be a little over-optimistic at times, to the point where their takes may not be as helpful for everyone. Additionally, there are certain opportunities or offers that just don’t fit into the scope their site. That’s why I’ve come to also enjoy sites such as Doctor of Credit and Frequent Miler, which tend to get a bit more granular. I also appreciate that those sites give more of their personal opinions — although you’re free to disagree with them (as I occasionally do). Both also have useful comment sections for the most part — but there are always exceptions, of course.

Speaking of comments, another place I’ve been finding myself spending more and more time as of late is Reddit. More specifically, the Amex subreddit where other users ask questions, share news, and discuss Amex-related matters. Yes, as I typed that, I realized just how nerdy it sounded.

Elsewhere, being a YouTuber myself, I’ve also found some great channels that have helped me navigate this world. One of my favorites so far has been Ask Sebby (who also has a pretty cool site). One of the things I like most about Sebastian is that he covers all kinds of topics, from specific timely offers to general info about different cards. By the way, I realized after the fact that I actually saw Sebastian at FinCon 2019 during a panel on credit cards — so that’s pretty cool

Although I’ve really enjoyed learning about travel hacking and award travel, there’s no doubt that I still feel a bit intimidated and overwhelmed. At the same time, I’m confident that my savviness in finding stackable deals and offers in the past could certainly come in handy here. Plus, now that I’ve accumulated a decent number of points, I can start scouting real deals and execute on actual bookings rather than operating in the theoretical.

As always, I’ll be sure to keep you updated on this part of my financial journey.

Author

Kyle Burbank

Founder ~ Moneyat30

Kyle is a freelance writer - including being the head writer for Fioney.com. He also serves as editorial director for the Disney fan site LaughingPlace.com and the founder of Money@30.com. In 2015, Kyle and his wife Bekah moved from Los Angeles to Springfield MO in pursuit of greater financial freedom. Together, the pair enjoy travel, coffee, and spending time with their dog Rigby. Additionally, as of 2023, they become first-time homeowners.