Hacking my way to free travel—master the systems & brEAK glass ceilings
You’ve probably heard stories or scrolled through your Instagram feed watching people who have cracked the code on using their credit card points to travel the world endlessly…or sit in the front of the plane and sip on champagne – all for free. Go on, roll your eyes – as it DOES seem a little far-fetched – but the truth is there’s actually a way to hack the points system that’ll let you do the same.
But before I share exactly how you can fly for free – there’s a couple of noteworthy facts you’d be surprised to learn – and it’s got to do with men, finances, and the patriarchy.
Now a quick detour on liberating femme financial freedom…
Living in NYC, on a $42,000 salary right in the middle of the 2007-2008 economic crisis made me realize that if I wanted to make travel a habit, I needed to come up with sustainable strategies to get me on the road without paying so much out of pocket – ushering in my identity of The Deal Seeking Diva among my friends. It was my mission to build a debt-free life of financial freedom and wealth, with travel at the center of it all – game on.
As a young woman in NYC looking to find a job during one of the greatest financial recessions, I was exposed to the narratives of not only the harmful gender salary gap, but also the systemic gender wealth gap that had transpired for generations. It wasn’t until the 1960s that women could open their own bank account without permission of their husbands. And we weren’t even 35 years out from the 1974 Equal Credit Opportunity Act that allowed women to open up a credit card in their own names without the bounds of gender discrimination. These, plus hundreds of years of financial repression have put women on the backfoot of equitable pay, job opportunities, and wealth building – all enablers for funding travel.
Given the financial inequities that women face, that hasn’t stopped me from working on how I close the gap, travel the world, and build my own wealth. When the “man” and big corporations gave us a tool where we could turn money we’re already spending into rewards, it’s been my full intention to exploit the hell out of it. I’ve never seen points and miles as a gimmick, or something that is for “only certain people.” No sir, this is for me. And it's for you too. This resource is available for ALL of us to take the power of responsible credit, and turn that into a truly life changing valuable currency that we can now and further enrich our lives through travel paid using points and miles vs cash. And I’ll keep socking that cash into my life experiences, plus making real wealth possible.
Ok, so let’s connect this all to travel.
Imagine a world where women could pull the veil back on their credit card’s fine print and finally make the most of the mountain of bonuses they’re sitting on that usually remain dormant. Yeah, there’s a zillion ways to earn points and miles for free travel… but most people don’t have a clue how to use them.
Taking advantage of hacking the points & miles systems will change your entire travel experience–really your entire life.
Like my client Lauren S did in 2024 when she took six, week-long trips to places including Croatia, Italy, and Mexico using her points and miles she earned through everyday spending–and saving her tens of thousands of dollars.
Or when my former colleague and now client Danielle C engineered all of her wedding spending to maximize points and miles to later cover her five-figure honeymoon to Bora Bora and New Zealand.
Even for my client Julie S who gushed about saving $4000 on a single trip to Africa over the summer because I was able to get her on track to finally pull the right triggers to use those points in more efficient and cost-saving ways.
For people who tap into points, these stories are not uncommon. They just overcame the complexity of terms and conditions (there IS a way), the fears of “getting it right”, having the confidence to lean into points & miles vs cash, and they are now traveling the world for a whole lot less – on repeat.
How I became a Chief Points Officer & a Free Trips Expert
When you’re 10 years old, life should be careless, free, innocent, and full of joy. The time to relish in play, push the limits of bedtime, and have eyes wide open for a booming life ahead. Unfortunately, for me, at that age, my life was rocked with the wildly early passing of my mother. Travel ultimately became my escape, what I could count on for making me feel whole again, and the constant bright spot in my life. From grounding some of our final family memories with my mother at Disney World before she passed, to my dad taking us to Ohio to spend our first family Christmas without her with our cousins, and my grandparents making it a point to take us on annual vacations and cruises so that we always reignited our joy of adventure–travel has always been my therapy. Even this past year, when my father passed away unexpectedly, I looked to trips as what would heal my heart. I wouldn’t be me without it. I’m sure for many of you reading this who have experienced loss, travel has become a way to bring back hope and wonderment. I hope at any age, you can find the gift that getting out in the world can bring and living on behalf of the loved ones that cannot do the same.
And then voom, adulting, ew. I was hit with the rude awakening on the real cost of travel as a young adult and mama needed to figure out how to keep this going... if money wasn't at my disposal, I had to get creative... essentially ushering in my points and miles lifestyle.
MY 10 POINTERS TO TRAVEL FOR FREE…regularly
As someone who has become the Queen’s Gambit of hacking the free travel system, if I had to do it all over again here are 10 things I’d tell my younger self…and you:
Never use a debit card, but have a debit card mentality – literally almost every debit card doesn’t let you earn ANY BONUSES on your purchases. So that’s a TON OF OPPORTUNITY lost with every single swipe. Get a point-earning credit card, put every single purchase you can possible on that card, and only charge what you can repay each month.
Start with a credit card with a hefty sign up bonus so you can start with a solid amount of points to book a trip right away and feel the high of getting a trip with points vs cash. This sensation of not using cash on a trip will be what you want to do again and again.
Choose a credit card that offers flexibility vs going for loyalty. There are many credit cards that allow you to use the points on various airlines. Many times, transferring your points to international airlines you can get even more value than on US-based airlines or booking in travel portals. So don’t box yourself into a credit card with only one airline, especially in the early days of point-earning where you want earning coupled with flexibility for your destination.
Select a credit card that earns points on the top 3 areas you spend money on the most. Don’t get wooed by a point influencer who tells you “this is the hot new card.” It may be for them, but it could be a card that doesn’t match your spending. The worst thing is having a card that doesn’t match how you spend money. You want to choose a card that earns points on the things you’re going to spend your money on already. For example, if you are someone who spends the most money on dining out, groceries, and ride-sharing, it’s best that you select a card that will give you most for those categories. An American Express Gold card gives you 4X for every dollar spent on Worldwide Restaurants & U.S. Supermarkets. Imagine if you’re only getting 1pt for every dollar, you could quadruple your point earning by moving to a card like this.
If you pay rent, having a Bilt credit card is non-negotiable. I wish I had gotten this card sooner because rent is one of my largest expenses each month. And to not earn points for this major expense is leaving so many points on the table. This card allows you to pay your rent and get points for it, literally giving you a way to earn thousands per month.
Set up frequent flier and hotel loyalty accounts immediately and attach your numbers to earn on every single trip you book. Even if you don’t travel often, every single point adds up and you will use them one day.
Don’t hoard points and miles. Airlines, credit cards, and hotels devalue the redemptions each year. Most people sit on those points thinking, “I’ll use them one day” not realizing they are literally throwing value away year over year. USE THEM like you would cash, and take the cash you would have spent otherwise and put that into a high-yield saving account or IRA and have your real money grow while you use points to travel.
Earn points in places you didn’t realize were possible. Whether it’s linking your favorite airline program to Uber or Lyft. Using a miles-earning shopping portal to earn miles for online shopping like Skymiles Shopping. Or linking your cards to Marriott’s Eat Around Town program to earn Bonvoy points when you dine at participating restaurants, there are literally tons of extra ways to earn points for things you’re already doing in your life.
Point transfers go the distance. People will ask me, “why don’t you use a card with cash back?” Well, those are typically fixed percentages and many up to 5% on purchases. And when you transfer points, you can get offers with much greater ROI. Airlines and hotels are notorious for giving big bonus transfers. Last holiday season, Virgin had an offer giving you a 40% bonus when you transferred your Amex Membership Reward points to Virgin–this smokes that 5% cash back any damn day. Especially when you can get one-way legs from the US to London for as low as 10,000 points on Virgin, this deal is legit. And going on now til the end of March, Chase has a 50% transfer offer for Marriott Bonvoy points. That means right now if you have Chase Ultimate Reward Points, and you transfer 20,000, you will get 30,000 total with that 50% transfer bonus! That’s a huge advantage on making the most of your points and miles.
Set Google Alerts to get your points back when fares fall. People constantly ask me, “how do you continuously travel on points so often?” Well, I’m always replenishing piggybank to keep using them. For example, since so many award trips are dynamically priced now, after you book a trip on miles, visit Google Flights, search the flights you booked on points or miles and set a Google Alert for that itinerary. When that flight has price changes you will be alerted. If you notice that the price went down, oftentimes, the price you paid with points/miles fell too. You can go back to the airline and request those miles back or cancel and rebook at the better price and re-bank those points/miles. Win win.
…and again, always use credit responsibly. Like literally, never sign up for a credit card bonus or overspend on it to earn a benefit. You are only turning what you CAN afford into a reward. Capeesh?
Alright, let’s get real
At the end of the day, remember, so many of the travel influencers in your feed/inbox care more about the credit card brands and travel programs, and less about you. I’ve watched so many influencers constantly push the “hottest” card or bonus, and meanwhile so many of those don’t have any relevance to their audience–ultimately having them feel they’re handcuffed to points and can’t figure out how to travel with them. No bueno.
My forever PSA: credit responsibility
Imagine you picked a card at their recommendation that doesn’t work well for the airlines you have access from your local airport or for the things you spend your money on? If you don’t dine out, why get a card that earns at restaurants? If you don’t have a car, why pick a card that earns on gas? You’d be limiting your earning potential or limiting ways to redeem for travel. It’s super important that you consider where you live, what you spend your money on, and where you want to go, and pick the card that aligns with you personally.
Free travel for all those who can’t
Today I’m the same age my mother was when she passed. Standing here with more money in my pocket and a rich life of travel, I’m proud and thrilled to know that I can see the world in a way she never had the chance. By mastering how to make the most of credit card bonuses, over the last decade I’ve scored 200+ flights to 35 countries, banked dozens of hotel stays, week upon weeks of car rentals, saving me six figures worth in travel. Yes, even my $30,000 9-day honeymoon to the Maldives flying business class and staying at the W Maldives was all covered using points and miles. It’s something I’m extremely proud of and hope to make a reality for many more women as they enrich their lives trekking the world. Something that I know my mom and all the women who came before me who didn’t have this opportunity would look down on fondly from above.
With that, I rally you to make 2025 the year that you stop thinking the benefits of points and miles are for someone else, and become someone who reaps the rewards of a world of free travel. If you want that level of points mastery, and get REAL serious about traveling the world for free, then that’s what you will get with Case & Points. Sign up for my FREE mini video series course and let’s optimize your wallet, maximize your earning, and match it all to your travel goals so you can travel the world for free more often. Better yet, take advantage of 2024 one-on-one coaching pricing before the end of March 2025 when I take my prices up a notch.
Simply email me at thecaseandpoints@gmail.com and say I want in on 2024 pricing and let’s get started!
Happy point hacking!
~Alicia
Your Chief Points Officer
