After reading the Frequent Flyer Master guide in December 2010, I scored two $20 tickets to Honolulu. Travel hacking was amazing, and I was hooked.
But a lot has changed since then. My wife Megan and I now have two children. During working hours—which is to say waking hours—I split my time between a startup called Closeup.fm, and the marketing consultancy that pays my bills, Wunderbar LLC.
Getting free stuff is exhilarating, but if you’re not careful, you can become a junkie. While chasing the buzz, you can turn the points and miles hobby into a part-time job. Believe me: I’ve made plenty of trips to our local mall to buy gift cards before hitting up several Walmarts to drain them on the way home.
Gas costs money. Duh. And more importantly, travel hacking requires time, creativity, and attention. I don’t have as much free time as I once did, and travel hacking thus has a real opportunity cost: What if I spent the same amount of time I focus on travel hacking doubling down on a business idea?
Could you spend your time making more money than travel hacking is saving you?
Now I recognize that travel hacking is a hobby, something I pursue simply because it’s fun. You don’t have to take a pragmatic, cold-blooded, money-making (or time-losing) attitude toward something that brings you pleasure. This hobby can reward you with bucket list adventures, once-in-a-lifetime vacations, unforgettable experiences—if you learn how to manage it.
This post won’t cover which credit card is the best or which Chase Ultimate Rewards transfers offer the most bang for your buck. You can find those tips elsewhere. No, this post will cover the system that I use to manage travel hacking so that it doesn’t become a burden.
Travel hacking is more rewarding if you can manage the hobby more effectively. Below are 17 travel hacking tips that will save you time and keep you sane.
Maybe you’re like me, and you want a hobby, not a huge time suck. You want to experience breathtaking places with family and friends, not squat on a huge cache of miles and points. You want to watch the sun set over the caldera from Mystique in Oia, Santorini, Greece.
That brings me to my first bit of advice, which is by no means original to me: earn and burn.
1) Earn and burn.
Points and miles won’t do you any good until you convert them into beautiful memories. Here’s why I think you should spend them now, not later:
- Airlines and hotels devalue redemptions all the time. Get while the gettin’s good.
- You don’t know what’s going to happen tomorrow. We live in a crazy world. Don’t hoard your travel hacking resources. Spend them. Enjoy them.
- You can always get more. Sure, the credit card products will change, the banks and financial institutions will close the loopholes and tighten restrictions, and yet, you’ll still have opportunities to hack the system. Loyalty programs are here to stay, and hotels and airlines bank on the fact that people will hoard rewards while exercising extreme caution. Do none of the above, and you will beat the system.
- Travel begets travel. The more you experience, the more you’ll want to experience. Burn those precious points and miles, and you’ll give yourself an incentive to drum up more. It’s as simple as that.
My travel hacking exploits have funded a triumphant parade of (almost) free plane tickets and hotel nights:
- A babymoon to Playa del Carmen, Mexico, which was 93% off
- A couple’s getaway to the U.S. Virgin Islands
- Family vacation in the Dominican Republic
- Reconnecting with friends in England & Scotland
- Speaking at a conference in Sweden
- Attending WDS in Portland, Oregon
Travel hacking has also put me in a position to help friends and family and pursue various business opportunities:
- Sending my friends Hope and John on a honeymoon to Belize
- Booking an award ticket to Hawaii for my parents
- Booking Southwest flights from Los Angeles for my younger sister and brother-in-law so that they could afford to vacation with us in Florida
- An award flight to MusicTech Conference in San Francisco, as well as flights to meetings with investors in Los Angeles, Denver, and Fort Lauderdale
I understand aspirational rewards. You want to fly in a first-class Emirates suite? Go for it. We play a game that pays out in champagne and caviar.
But don’t delay your gratification for too long because life happens. You get married, have kids, or buy a house. Before you know it, demands on your time grow, and availability in your calendar shrinks.
So force your own hand, and book the first leg of your journey.
2) Pick a place.
The intricacies of travel hacking—and they’re there, believe me—will melt your brain if passion for a real place doesn’t compel you. Where do you want to go?
It doesn’t matter if your dream destination is Phoenix, Disney World, or even Siberia. Just pick a place that you want to visit or explore because any destination will do in order to get you started. If you haven’t already, write down a list of places in Evernote or in your journal. Prioritize them. Pick one.
3) Check your calendar and pick travel dates that will give you enough lead time.
Travel is supposed to be fun, so if you’re new to traveling be wary of setting something up without giving yourself plenty of time to prepare for it. For example, in December 2015, I started planning a trip to Greece for August 2016. There’s nothing that can ruin your adventure faster than not being better prepared.
4) Nail down travel dates with your first booking.
When we were planning for our trip to Greece, I found a direct flight from JFK to Athens. I was quick to put the award tickets on hold for 24 hours and then discussed the itinerary with my wife.
In a certain respect, Delta chose dates for us. We couldn’t do much better than Delta One business class from JFK to Athens: 180-degree flat-bed seats with Westin Heavenly® In-Flight Bedding, TUMI amenity kits, and Kiehl’s products. The retail price of each seat was $6279.80, but, in the end, we only ended up paying 62,500 miles and $5.60 each.
Delta’s award availability was the nudge we needed to not overthink the decision.
5) Add travel dates to your calendar.
Go ahead and ask for time off at work. If you have to wait until closer to your departure date, then add an Ask Off Work reminder to your calendar. If you’re self-employed, begin making the necessary arrangements and start saving money.
Blocking out the dates in your calendar helps to make the trip real. It sets the planning in motion, and the more time you invest, the less likely you’ll be to bump the trip if you later have a conflict. Put your own goals first.
Thankfully, Megan and I had plenty of time to find a babysitter!
6) Pick your travel companions.
I know plenty of people who love traveling solo. Chris Guillebeau visited every country in the world, and he took many of those trips alone. Matthew Karsten, the Expert Vagabond, travels solo full-time.
While I enjoy solo travel in small doses, I enjoy traveling with my wife, Megan, even more. My Closeup.fm co-founder Nathan Fray is another excellent travel companion. If you enjoy traveling solo, then do what works for you, but I find that experiences are just more meaningful for me if I share them with others. And I don’t think I’m alone in this. (See what I did there?)
Which of your friends or family members love to travel? Which ones do stuff, and by “do stuff” I mean make a plan and actually execute it? Invite one or two of these people to take the journey with you. Planning the journey is half the fun of traveling with someone else! Together you can discuss the hotels you might stay at, or suss out the perfect Airbnb spot.
7) Pick a travel style.
Everyone prefers to travel differently – what is your travel style? Do you prefer to fly in first-class or coach? Are you more likely to couch surf so that you can save money or splurge on boutique hotels? Are you content with cheap sandwiches and watery beer or is your vacation not quite a vacation without exquisite meals at restaurants with Michelin stars?
Do you dream about sunbathing or skydiving? Focus on what revitalizes your heart, mind, and soul. There is no one size fits all vacation.
For our trip to Greece, we spent 125,000 Delta miles to get us from JFK to ATH, and 140,000 United miles to go from Frankfurt to Washington, D.C., but so what? We had them, so we might as well have used them the way we wanted to. What I really wanted were lie-flat seats in Business class for us, and I thought it would be so cool to fly in one of Lufthansa’s 747s on the upper deck. Sure, we could have flown economy and conserved miles, but I wanted to go all out.
After all, this was my wife and marriage we were talking about! It’s okay to be glamorous for a couple of weeks.
What’s your dream? Don’t be afraid to spend serious miles, points, and coinage to pursue a dream. Thriftiness is only a virtue until you’re just being cheap.
8) Plan backward from your destination and departure date.
How will you handle airfare, transportation, lodging, food, attractions, budget, and packing? This might surprise you, but according to a study from the Netherlands, simply planning for the vacation can increase most people’s levels of happiness.
But all of that planning can be hard to decipher and utilize later if you don’t stay organized, and that happiness can quickly turn into anxiety.
You don’t have to memorize the arcane terminology or dig up obscure travel hacking tactics in order to plan a trip—unless you really want to. The key to staying sane and enthusiastic about a trip boils down to organization. It’s really that simple. Certain tools can help you stay focused and will simplify and enrich the planning process:
- Google Sheets for non-sensitive credit card information
- LastPass for log-in credentials
- Award Wallet for miles and points balances
- Trello for travel hacking task management
- ExpertFlyer for award ticket searches
- Google Flights for exploring options and building itineraries
- Routehappy for comparing airlines flying the same route
- Seatguru for picking the best seats
- TripAdvisor for restaurant recommendations
- Dropbox for storing receipts, vouchers, et al
- Evernote for saving tips and notes about your destination(s)
- Google Sheets for capturing your complete itinerary as you build it (flights, hotels, confirmation numbers, miles/points spent, dollars spent, check-in requirements, check-in links)
Apply similar organizational practices you use every day to help make traveling less stressful. If you always put your keys in the same place, you’re less likely to lose track of them. Traveling is no different! Always keeping your travel related items in the same place frees up your mind and allows you to enjoy your trips – which is what it’s all about in the first place.
9) Research new credit cards that fit into your dream and apply, as needed.
For example, if Google Flights tells you that Delta offers a direct flight from your airport to Seattle, then you might take a closer look at the Gold Delta SkyMiles Card, or the Starwood Preferred Guest AmEx that lets you convert SPG points into Delta miles. These resources are readily available to you, so you might as well use them in a way that best suits your needs and desires.
10) Meet the minimum spend requirement on your new card.
Try to avoid going down the “manufactured spending” rabbit hole, where you drive around in search of gift cards before redepositing them in your account. Yes, it works, but it can take a lot of time.
Instead, focus on spending as much as you have to spend in order to get that first sign-up bonus. Put all of your regular expenses on the card, ask friends to help you out by putting their big purchases on your card and reimbursing you, and read a few blog posts if you still need ideas. Do what you have to do, but ultimately, stay focused.
11) Set calendar reminders to ensure that you pay your balances in full.
On-time payments keep your credit score in shipshape and ensure that the free miles or points bonus does not end up becoming expensive due to late payment or interest charges.
I typically pay my balance once a week to ensure that we don’t overspend on the card and accidentally blow our budget.
12) Book flights, hotels, and car rentals with miles, points, or cash as the situation warrants.
I always set a goal for myself: save as much money out-of-pocket as possible while staying true to the dream. In college, I spent an amazing semester in Vienna, but up until recently I hadn’t been back since. Travel hacking made it possible for me to change that.
Though I could have used a free night certificate to book a room at the InterContinental while I was there, I had my heart set on a view of Die Oper and Stephansdom. Naturally, I bit the bullet and paid cash for The Guest House, and I’m so glad that I did.
13) Use your arsenal of credit cards to save money where you can, earn more points and miles, and create a virtuous cycle.
For me, the end goal is never penny-pinching. The fact is, we don’t have to spend money on any of this. We didn’t have to go to Greece at all.
No, the beauty of travel hacking is that it enables you to save money so that you can spend it on what you truly value. Here are highlights from the Greece trip:
- I used the Cash & Points option to book a room at the King George in Athens.
- American Express Membership Rewards got us a free night at Kivotos, and I paid out of pocket for the second.
- I used AutoEurope to book a car rental because they give you an iron-clad voucher to help circumvent any weirdness or surprise fees at the rental desk. (Hat tip to my brilliant friend Gabi Logan for her extensive knowledge of Greece.) I’ll rely on my Chase Sapphire Preferred for free primary rental insurance.
- We stayed two nights at Mystique, and I paid cash for both—even though we could have stayed for (or much more cheaply) elsewhere.
- ThankYou Points bagged us a free room at Chromata Up-Style Hotel.
Save money for travel so that you don’t have to worry about it while traveling. Here are some options available to you that I especially like:
- Smartypig for automating savings with recurring withdrawals
- Aspiration Checking for 1% APY and no ATM withdrawal fees around the world
- Digit for saving even more money without thinking about it
15) Nail down your repeatable process.
While we were in Greece, we started to discuss the big trip we want to take next year. Hawaii again? Scotland? Australia, Brazil, or Thailand?
And as soon as we got back, I started planning the next trip. (Okay, full disclosure: I had already started looking at Flying Blue award flights to Lihue, Kauai before we left for Greece.)
In a similar fashion, if you run through the same process anytime you want to accumulate points and miles for a new trip, you’ll avoid headaches (“I can’t believe I forgot to meet the minimum spend on that new card!”). You’ll make fewer mistakes (“I can’t believe forgot to pay off that credit card!”).
Travel hacking takes some legwork, but it’s not hard the way running a marathon is hard.
Follow instructions once, and you have used a plan. Use the plan multiple times, and you’re now following a process.
16) Spend your credit.
Any mention of leveraging CREDIT gives most people heartburn. Why? They have digested a lot of misinformation. Credit has these vague but visceral negative connotations. It’s “bad” though people usually can’t explain why.
They have a hard time believing me when I tell them that in 2015 I signed up for 12 new credit cards and racked up over 1.3 million points and miles. When I tell them that my credit score also passed 800 for the first time, their jaws drop. “But, but… that doesn’t make any sense,” they say.
I shrug. “I don’t know what to tell you except that most of what you’ve learned about credit probably isn’t true.”
Your credit is not something you should abuse. To the contrary, credit is something that you want to understand, steward, and invest. I choose to invest my credit (temporarily) in new credit cards. Each hard inquiry costs me a couple of points, but those typically impact your score only for 12 months and they roll off your credit report after 24.
A short-term drop in my credit score is a perfectly reasonable trade for a sizable sign-up bonus on a new credit card.
17) Improve your credit score.
Credit is generally not a good topic to bring up at parties. But good credit offers a variety of benefits:
- Better home loans
- Better car loans
- Better insurance rates
- Better impression with potential employers
- Better interest rates on credit cards
Do you see a trend?
The higher your credit score, the more of it you can “spend” on travel hacking without seeing any adverse effects (assuming of course that you don’t accumulate a bunch of debt!).
Here is how to plan your next trip:
- 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.
- Nail down your repeatable process.
- Spend your credit.
- Improve your credit score.
That’s it! You can go as far down the travel hacking rabbit hole as you like, but even if you stick to the basics outlined above, you can go anywhere in the world.
Editor’s Note: Get A Free Course on Better Credit
I really appreciate Austin sharing SO MUCH detailed info with us. I know from many emails that some of you would like to beef up your credit knowledge, and you’d like to do that without wading through a ton of posts and forums. Good news: Austin has put together a free, 10-lesson course called “Better Credit in 10 Days.” The email course will walk you through credit basics, as well as the best ways to boost your score in a short period of time.