This is a special post from Austin Church in Knoxville, Tennessee.
Back in December 2010, inspired by the Frequent Flyer Master guide, I snagged round-trip tickets to Honolulu for just $20 each. That’s when I truly understood the magic of Travel Hacking, and I was instantly captivated.
However, the landscape of travel hacking has evolved significantly since then. My life too, has changed. My wife Megan and I are now parents to two wonderful children. My working hours – essentially my waking hours – are divided between a startup, Closeup.fm, and my marketing consultancy, Wunderbar LLC, which is my primary source of income.
The thrill of getting things for free or heavily discounted is undeniable. Yet, it’s a slippery slope. If you’re not careful, the pursuit of points and miles can become an all-consuming obsession, morphing from a hobby into a part-time job. I speak from experience here, having spent countless hours driving to malls to purchase gift cards, followed by multiple trips to different stores to liquidate them.
Gasoline isn’t free, and more importantly, travel hacking demands a significant investment of time, creativity, and focus. Time, a resource that’s become increasingly precious for me. This realization brought me to a crucial question: Could the time I dedicate to travel hacking be better spent on activities that generate more income or contribute to my business growth?
COULD YOUR TIME BE MORE PROFITABLY INVESTED THAN IN TRAVEL HACKING?
I’ve come to recognize that travel hacking is, at its core, a hobby—something I engage in because I genuinely enjoy it. It’s not always about cold, hard pragmatism or solely focusing on the monetary (or time) cost-benefit analysis of activities that bring joy. This hobby has the potential to unlock incredible, once-in-a-lifetime travel experiences, fulfilling bucket-list adventures and creating unforgettable memories, provided it’s managed effectively.
This article isn’t another guide on the “best travel credit card” or which points transfers offer maximum value – you can find countless resources covering those topics. Instead, I want to share the system I’ve developed to manage travel hacking in a way that enhances my life rather than becoming a burden.
Travel hacking becomes truly rewarding when it’s managed efficiently. Here are 17 travel hacking tips designed to save you time, preserve your sanity, and maximize your travel experiences.
Perhaps you, like me, seek a fulfilling hobby that doesn’t devour your time. You want to explore breathtaking destinations with loved ones, not just accumulate a massive, unused stockpile of points and miles. You envision yourself witnessing the sunset over the caldera from Mystique in Oia, Santorini, Greece.
This leads me to my first, and by no means original, piece of advice in the world of travel hacking: embrace the “earn and burn” philosophy.
1) EARN AND BURN.
Points and miles are essentially worthless until you convert them into tangible experiences – beautiful memories. Here’s why I firmly believe in spending them sooner rather than later:
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Frequent Devaluations: Airlines and hotels frequently devalue their rewards programs. Redemption values can decrease with little to no notice, meaning your points become worth less over time. Strike while the iron’s hot.
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Life is Unpredictable: The future is uncertain. Don’t hoard your travel hacking resources as if they are an investment account. Use them. Enjoy them. Life is for living now.
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Opportunities Abound: You can always earn more. While credit card offers and loyalty program rules will inevitably change, and banks may tighten restrictions, new opportunities to hack the system will always emerge. Loyalty programs are a permanent fixture in the travel industry, and they rely on the fact that many people hoard rewards excessively. By actively earning and spending, you leverage the system to your advantage.
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Travel Inspires More Travel: The more you explore, the more your wanderlust grows. Burning your points and miles creates a positive feedback loop, motivating you to replenish your balances and plan your next adventure. It’s a self-perpetuating cycle of exploration and reward.
My personal travel hacking journey has funded an incredible array of (almost) free flights and hotel stays:
- A pre-baby getaway to Playa del Carmen, Mexico, at 93% off.
- A romantic escape to the U.S. Virgin Islands.
- A memorable family vacation in the Dominican Republic.
- Reconnecting with friends in England & Scotland.
- Speaking engagement at a conference in Sweden.
- Attending WDS in Portland, Oregon.
Travel hacking has also empowered me to extend generosity to loved ones and pursue business opportunities:
- Sending friends Hope and John on their honeymoon to Belize.
- Booking award flights to Hawaii for my parents.
- Securing Southwest flights from Los Angeles for my sister and brother-in-law to join our family vacation in Florida.
- Award flight to the MusicTech Conference in San Francisco, along with flights for investor meetings in Los Angeles, Denver, and Fort Lauderdale.
I understand the allure of aspirational redemptions, like flying in an Emirates First Class suite. If that’s your goal, go for it. Travel hacking can indeed unlock those premium experiences.
However, avoid delaying gratification indefinitely. Life evolves rapidly. Marriage, children, homeownership – these milestones shift priorities and shrink available time.
Take control and initiate your journey by booking that first flight.
2) PICK A PLACE.
The intricacies of travel hacking can become overwhelming if you lack a genuine destination to fuel your passion. Where do you truly want to go?
Whether your dream is Phoenix, Disney World, or even Siberia, the specific location is less important than having a destination in mind to kickstart your planning. If you haven’t already, create a list of desired destinations in a note-taking app or journal. Prioritize them. Then, select one to focus on.
3) CHECK YOUR CALENDAR AND PICK TRAVEL DATES THAT WILL GIVE YOU ENOUGH LEAD TIME.
Travel should be enjoyable, especially for newcomers to travel hacking. Avoid setting yourself up for stress by planning a trip with insufficient preparation time. For instance, in December 2015, I began planning a trip to Greece for August 2016. Adequate lead time is crucial to prevent your dream adventure from turning into a logistical nightmare.
4) NAIL DOWN TRAVEL DATES WITH YOUR FIRST BOOKING.
When planning our Greece trip, I discovered a direct flight from JFK to Athens. I promptly placed the award tickets on hold for 24 hours and discussed the itinerary with my wife.
In a way, Delta Airlines guided our dates. The opportunity to fly Delta One business class from JFK to Athens was too good to pass up: 180-degree flat-bed seats with Westin Heavenly® In-Flight Bedding, TUMI amenity kits, and Kiehl’s products. These seats retailed for $6279.80 each, but we secured them for just 62,500 miles and $5.60 per person.
Delta’s award availability provided the perfect impetus to finalize our dates and stop overthinking the details.
5) ADD TRAVEL DATES TO YOUR CALENDAR.
Request time off work immediately. If you need to wait, set a calendar reminder to request time off closer to the date. If you’re self-employed, begin making necessary arrangements and allocate savings.
Blocking out dates on your calendar makes the trip feel real and sets the planning process in motion. The more you invest in planning, the less likely you are to postpone the trip if conflicts arise later. Prioritize your own goals.
Luckily, Megan and I had ample time to arrange for childcare!
6) PICK YOUR TRAVEL COMPANIONS.
Many people enjoy solo travel. Chris Guillebeau famously visited every country in the world, often traveling alone. Matthew Karsten, the Expert Vagabond, travels solo full-time as a lifestyle.
While I appreciate solo travel in small doses, traveling with my wife, Megan, is far more rewarding. My Closeup.fm co-founder Nathan Fray is also an excellent travel companion. If solo travel is your preference, embrace it. However, I find that shared experiences amplify joy. And I believe many others feel the same.
Consider inviting friends or family who share a passion for travel and are proactive planners. Planning the journey together is a significant part of the enjoyment of traveling with others. Discuss potential hotels or scout perfect Airbnb locations together.
Deciding between the Grand Bretagne and King George hotels in Athens was enjoyable, but sharing cocktails with Megan while admiring the Acropolis view was priceless.
7) PICK A TRAVEL STYLE.
Travel styles are deeply personal. Do you prioritize first-class flights or are you comfortable in economy? Do you prefer budget-friendly couch surfing or indulging in boutique hotels? Are you content with simple meals or do Michelin-starred restaurants define your vacation experience?
Do you dream of relaxing on beaches or adrenaline-pumping activities like skydiving? Focus on what truly rejuvenates your mind, body, and spirit. There’s no universal “right” way to vacation.
For our Greece trip, we used 125,000 Delta miles for JFK to ATH and 140,000 United miles for Frankfurt to Washington, D.C. We had the miles, so we used them to create our desired experience. My priority was lie-flat business class seats, and I was excited to fly on the upper deck of a Lufthansa 747. We could have flown economy and saved miles, but I wanted to maximize comfort and enjoyment.
After all, this was a special trip with my wife. It’s perfectly acceptable to embrace a bit of luxury for a well-deserved vacation.
What is your dream travel style? Don’t hesitate to invest miles, points, and even cash to pursue your vision. Thriftiness is valuable, but avoid being penny-wise and pound-foolish when it comes to experiences that matter.
8) PLAN BACKWARD FROM YOUR DESTINATION AND DEPARTURE DATE.
Consider all aspects: airfare, transportation, lodging, food, activities, budget, and packing. Interestingly, a study from the Netherlands indicates that simply planning a vacation can increase happiness levels for many.
However, disorganized planning can quickly transform excitement into anxiety.
You don’t need to master complex terminology or obscure travel hacking tactics unless you truly desire to. The key to stress-free and enjoyable travel planning is organization. It’s that simple. Utilize tools to stay focused and streamline the process:
Apply your everyday organizational habits to travel planning. Just as keeping your keys in a designated spot prevents losing them, maintaining order with travel items and information frees your mind to enjoy the journey itself.
9) RESEARCH NEW CREDIT CARDS THAT FIT INTO YOUR DREAM AND APPLY, AS NEEDED.
For instance, if Google Flights shows a direct Delta flight to Seattle, explore Delta-affiliated cards like the Gold Delta SkyMiles Card or the Starwood Preferred Guest AmEx, which allows points transfer to Delta. These resources are readily available; use them strategically to align with your travel goals.
10) MEET THE MINIMUM SPEND REQUIREMENT ON YOUR NEW CARD.
Avoid the “manufactured spending” rabbit hole – driving around buying gift cards and then liquidating them. While effective, it’s time-consuming.
Instead, focus on meeting the minimum spending requirement organically to earn the valuable sign-up bonus. Put regular expenses on the card, ask friends to put large purchases on your card and reimburse you, and consult blogs for additional ideas if needed. Do what’s necessary, but stay focused on efficient spending.
11) SET CALENDAR REMINDERS TO ENSURE THAT YOU PAY YOUR BALANCES IN FULL.
Timely payments are crucial for maintaining a healthy credit score and ensuring that your “free” miles and points don’t become costly due to interest or late fees.
I typically pay my credit card balances weekly to proactively manage spending and avoid exceeding our budget.
12) BOOK FLIGHTS, HOTELS, AND CAR RENTALS WITH MILES, POINTS, OR CASH AS THE SITUATION WARRANTS.
My personal goal is to minimize out-of-pocket expenses while realizing my travel dreams. During college, I spent a semester in Vienna but hadn’t returned until recently. Travel hacking enabled me to revisit this cherished city.
While I could have used a free night certificate at the InterContinental, I desired a specific view – overlooking Die Oper and Stephansdom. I chose to pay cash for The Guest House, and it was absolutely worth it.
13) USE YOUR ARSENAL OF CREDIT CARDS TO SAVE MONEY WHERE YOU CAN, EARN MORE POINTS AND MILES, AND CREATE A VIRTUOUS CYCLE.
My ultimate aim isn’t just about being frugal. We didn’t have to go to Greece.
The true power of travel hacking lies in its ability to unlock savings that can be redirected towards experiences you genuinely value. Highlights from our Greece trip included:
14) BUDGET.
Save proactively for travel so that financial concerns don’t overshadow your trip. Here are effective budgeting approaches I recommend:
15) NAIL DOWN YOUR REPEATABLE PROCESS.
During our Greece trip, we began discussing our next major adventure. Hawaii again? Scotland? Australia, Brazil, or Thailand?
Upon returning home, I immediately started planning the next trip. (Full disclosure: I had already begun researching Flying Blue award flights to Lihue, Kauai, before we even departed for Greece.)
Similarly, establishing a repeatable process for earning points and miles for each new trip minimizes errors (“I can’t believe I missed the minimum spend!”) and oversights (“I forgot to pay the credit card bill!”).
Travel hacking requires effort, but it’s not inherently difficult like running a marathon.
Following instructions once is using a plan. Using that plan repeatedly transforms it into a process.
16) SPEND YOUR CREDIT.
The mere mention of leveraging CREDIT often causes anxiety. Why? Misinformation is rampant. Credit carries a vague but negative connotation – it’s considered “bad,” though often without clear justification.
People are often skeptical when I share that in 2015, I signed up for 12 new credit cards and accumulated over 1.3 million points and miles. When I mention that my credit score simultaneously surpassed 800, they are astonished. “But… but that doesn’t make sense,” they exclaim.
I simply shrug. “Most of what you’ve learned about credit is likely inaccurate.”
Credit isn’t something to abuse. Instead, it’s a tool to understand, manage, and strategically invest. I choose to invest my credit (temporarily) in new credit cards. Each credit inquiry causes a minor, temporary dip in my score, but this is a reasonable trade-off for substantial sign-up bonuses.
A short-term credit score fluctuation is a worthwhile exchange for the long-term benefits of travel rewards.
17) IMPROVE YOUR CREDIT SCORE.
Credit scores aren’t typical party conversation starters. However, a strong credit score offers significant advantages:
- Favorable home loan rates.
- Better auto loan terms.
- Lower insurance premiums.
- Positive impression with potential employers.
- More advantageous credit card interest rates.
Notice a pattern?
The higher your credit score, the more effectively you can leverage credit for travel hacking without negative consequences (assuming responsible debt management!).
LET’S REVIEW.
Here’s a recap of how to plan your next trip using travel hacking effectively:
- Earn and burn.
- Pick a place.
- Check your calendar and pick travel dates that will give you enough lead time.
- Nail down travel dates with your first booking.
- Add travel dates to your calendar.
- Pick your travel companions.
- Pick a travel style.
- Plan backward from your destination and departure date.
- Research new credit cards that fit into your dream and apply, as needed.
- Meet the minimum spending requirement on your new card.
- Set calendar reminders to ensure that you pay your balances in full.
- Book flights, hotels, and car rentals with miles, points, or cash as the situation warrants.
- Use your arsenal of credit cards to save money where you can, earn more points and miles, and create a virtuous cycle.
- Budget.
- Nail down your repeatable process.
- Spend your credit.
- Improve your credit score.
That’s it! You can delve as deeply into the world of travel hacking as you desire. Even sticking to these fundamental tips can unlock travel to destinations around the globe.
EDITOR’S NOTE: GET A FREE COURSE ON BETTER CREDIT
I deeply appreciate Austin sharing such comprehensive and detailed information with us. Based on numerous emails, I know many of you are interested in enhancing your credit knowledge without sifting through countless posts and forums. Great news: Austin has created a free, 10-lesson course called “Better Credit in 10 Days.” This email course provides a clear walkthrough of credit basics and effective strategies to boost your score quickly.
