Unfortunately for me, I have expensive tastes.
This is reflective in my very odd, and slightly pretentious quests of visiting the best golf courses in the world, the best bars in the world, and continuing to make progress on my bucket list as much as I can.
For the average person, you’d look at these things and say “there’s no way I could do this! You’d have to be a millionaire to be able to afford all of these activities and the travel associated with it.”
Historically, that may be true.
But if you’re a reader of this blog, then there’s a good chance you’re familiar with the concept of travel hacking.
What is Travel Hacking?
In the traditional sense, travel hacking is collecting credit card points and miles to get free or cheap flights, hotels, and rental cars for little to no money.
My bet is you’re already pretty familiar with this, and have possibly even read any number of countless other websites about this specific topic.
However, personally I’ve expanded this concept of travel hacking to include building brands that create win/win scenarios for you and the companies you work with, in order to provide them exposure, and you incredible experiences.
Would I be able to play the top 100 golf courses in the world without having Breaking Eighty to leverage? Certainly not at this point in my life.
However, we’ll save the expanded stuff for another time. (If you’re interested, we’ve even devoted a whole course to that side of traveling. You can check out Hobby Hacking here.)
In doing all of this, one of the most common questions I get asked is how do you get so many travel deals?
In this post, I’m going to share with you the 5 travel hacks that have been most valuable for me in my life. These hacks have enabled me to take exotic trips, stay in 5 star hotels, and get upgraded flights – without having to spend a fortune to do so.
Check out my vlog on travel hacking from my room at the St. Regis in Singapore (yeah, you guessed it, paid for that one on points as well):
My 5 Best Travel Hacks that Save Me THOUSANDS Each Year
Considering I’ve spent very little time there, I have a surprising amount of content from Singapore.
There was the time we had a layover there on our honeymoon:
And the much more interesting story of how I used points to book a 17 hour flight that is traditionally one of the most expensive on Earth:
This latest trip to Singapore was the first time I actually went there to visit, not just stopping over.
8 of the top 100 bars in the world are there, and so my wife and I decided to take a trip to experience them!
But in doing this, it made me realize just how fortunate we are to be able to travel the way we do – especially considering it isn’t hard.
So here are some of my favorite travel hacks I leverage each year.
1) Sign up for a Chase Sapphire Reserve Credit Card
I should make something very clear, I’m not an affiliate for Chase, nor do I get paid any commission or bonus for telling you that.
I say it because the Sapphire Reserve is frankly the single best travel hack I know of.
Here’s the deal, most people are scared away by the $450 annual fee. But $300 of that is credited back to your account each year to reimburse for travel expenses.
Even if you don’t travel, you’ll have expenses that get qualified as such and get your money back. Think things like gas, parking, and other similar expenses.
So essentially it’s a fee of $150 a year.
What does that get you?
For starters, like with many cards you get a 50k point sign up bonus when you get the card and hit the minimum spend. That right there is enough for flights that can total over $1k.
You can transfer them to United (and book on other Star Alliance airlines), Hyatt (and get some pretty awesome hotel stays), or any number of other partners.
We used Chase points to book round trip business class flights on Lufthansa to the Maldives for our honeymoon.
On this most recent trip we transferred Chase points to Hyatt for a stay at the $717/night Park Hyatt Tokyo.
You get access to Priority Pass, which gets you lounge access to over 1,000 airline lounges across the world. This alone is worth that $150 fee, as not only does it make my travel more comfortable, but it saves me hundreds of dollars each year on food and drinks at airports.
You get 3x points on travel and dining out, which if you’re like me, can add up quickly.
They pay for your TSA-Pre as well.
And these are just the highlights among close to a dozen other benefits.
This one card is the best hack I know of, and if you have decent credit? Get it, pay it off every month, and roll in those sweet, sweet benefits.
2) Leverage the Chase Booking Portal
Historically my experience actually using credit card booking portals to directly book hotels or rental cars has been incredibly mediocre.
It’s nearly always more expensive than you might find on Expedia or another site, so it’s not worth it.
With the Chase travel portal, this is very much not the case.
Reminder: I’m not affiliate with Chase in ANY way. This is just what’s worked for me.
There are two things I specifically do that saves me a ton of money, and allows me to have nicer experiences.
1) Check their site for cheap rental cars
A couple years ago my friend Dan and I were doing a road trip through Scotland.
Here’s a video of us from our first trip to Scotland and us learning how to drive on the other side of the road:
The best deal I could find on an entirely average mid size rental car was about $700 through sites like Expedia and booking direct through the different rental car companies.
On a whim I logged into the Chase portal to see how much they’d charge.
Exact same dates?
Even better? Rather than a crappy Chevy Malibu, it was for a Mercedes E-Class wagon.
It worked perfectly, and it was all because of Chase. This isn’t a one of either. 80% of the time I look, it’s substantially less money than the traditional booking places.
A couple weeks ago I got a text from my friend Kyle who used it in Iceland saying:
“Dude you were totally right! This Chase deal for rental cars is insane!”
2) Use a Combo of Points and Dollars
I mastered this strategy when Tate and I were on our 2 month global sabbatical last year.
When I travel I usually have an idea of what I want to spend on a room per night.
I also have an idea of how nice of a place I want to stay in (usually it’s 5 star, I’m bougie like that).
But the thought of paying $250++++ a night for a hotel is just ridiculous to me.
When I login to Chase though, it will show me all the available hotels that fit my parameters, including many that have “specials” and then it allows me to use any combo of points and dollars that I’d like.
So this room at the St. Regis in Singapore? It was somewhere in the neighborhood of 25k points and $200 for the duration of our stay.
That makes the price much more palatable.
In the Sabbatical post above I shared that the best stories in life come on the far ends of the spectrum.
The dumpy $15 a night bungalow on the beach will come with a great story (I’ve had a lot of those over the years).
The ridiculous, over the top 5 star hotel, will also come with a story.
The random 2.5 star Ramada Inn? There’s no good story that will come out of that.
This is why I prefer to travel on these two ends of the spectrum.
3) Request an Airline Status Match
This is one that is for the more advanced traveler, but it’s worked for me in the past.
Most airlines will grant you a status match once every three years.
As an example, I used to have status on American Air.
But their flights out of Portland were well, pretty bad.
Super early flight times (I can’t tell you how many times I was on the 5am to Dallas), and most of the planes coming into Portland were the older US Airways planes (ie uncomfortable, with no benefits).
So I went to Delta and asked them if they’d match my status.
I had to fly 6500 miles in 3 months, and if so, they’d grant me status!
Worked like a charm, and because I did this after July 1st, my status was good for the entire next calendar year.
So if you think you’re not going to hit your status on one airline, but still have a couple trips coming up?
Request the status match and get an extra 18 months of upgrades, free checked bags, and priority boarding.
You can generally do this with each airline once every 3 years, so it’s feasible if you don’t have any true loyalty, you could continue bouncing around without having to fly nearly as much each year.
4) Sign up for Scotts Cheap Flights, Jetto App, and Others
There are a bevy of cheap flights, mistake fares, and other deals out there if you know where to look.
Chances are you’re not going to just stumble across some shockingly low international flight deals.
But if you pay attention to the people whose sole job it is to find those deals, then you can get some pretty cool opportunities.
Like Portland to China for less than $500.
Philly to Croatia for less than $400.
The list goes on an every week there are great deals to be had, so sign up for them to make sure you don’t miss out.
5) Be Deliberate About What Cards You Spend On
Most people have one credit card they use for just about everything. Maybe it’s an airline mileage card or a Capital One cash back card.
That’s fine, but if you really want to maximize your benefits you should be deliberate about what you’re spending and where.
For instance the Chase Sapphire Reserve has 3x points on travel and dining out.
Their Business Preferred Card pays 3x points on online advertising. This is what I use for my business expenses.
The new World of Hyatt card pays 2x points on Gym memberships.
The Delta Platinum will wave your dollar spend requirement for airline status if you spend more than $25k in a calendar year.
By simply being more deliberate with where you spend your money, you can get thousands of extra points and benefits each year.
Right now, I have three Chase cards I use for different things. By also sticking with one company, it means all of my points are going to the same place. So instead of having a handful of Amex, a handful of Capital One etc. I go almost all Chase, which adds up more than you think it will. Doing this makes spending them that much easier.
Bonus: Taking Travel Hacking One Step Further
I know earlier in this post, I said I wouldn’t go into much detail on the brand building part of travel hacking.
But it’s been honestly the most valuable part of my travel hacking experience, that I’d be remiss not to at least mention it.
Each of the brands I’ve built over the years have had a significant impact on my life in one way or another.
All of them have not only been successful businesses, but they’ve fundamentally brought joy and opportunities into my life that I simply wouldn’t have had otherwise.
And in many cases that has saved me thousands, if not tens of thousands of dollars.
For instance, I rarely pay for rounds of golf when I travel now. The one I played in Singapore had a retail price of over $300:
Just last week, I partnered with Lexus to attend an event they were hosting at Pebble Beach:
Bar tabs get comped when I’m on my quest.
Free products regularly show up on my doorstep to try out (with no strings attached).
So while in some cases these “hacks” have to do with travel, others get leveraged on a daily basis when I’m at home just working on my business.
Sure it might be a little more work than simply signing up for a credit card, but the payoff can be far greater, more fulfilling, and a win/win for everyone involved.
If this is something you’re interested in, members of our Location Rebel Academy Ultimate Package not only get access to our lively community forums, but they get every single product I’ve ever created.
This includes both the full Hobby Hacking course on how to build these kind of brands, as well as Hacking the High Life which goes in depth into both traditional travel hacking and how to leverage your new Hobby business in this way as well.
What travel hacks have worked best for you? Let us know in the comments!