The Art of Travel Hacking

When my wife and I got engaged one of the easiest decisions to make was on where to honeymoon- Italy.  We love the food, we love the wine, and neither of us had been.  Planning the trip only reinforced that decision, with the one caveat being that we’d need a solid 17 days to see the things we wanted to without feeling rushed.  The time commitment wasn’t the problem.  One of the benefits of being young, early in our careers, and sans any real reason possibility was the ability to take super long vacations.  The problem was paying for the trip. 

At the time, neither of us traveled much or had status of any kind, but we did have a wedding to pay for and decided that this would be the perfect time to enter the world of travel hacking.   Long story short, we did our 17 day trip with our only real expense being food.  And since that time, we’ve earned and redeemed well over a million miles.  The best part is that these miles have come with little effort, and while my work travel has picked up significantly in recent years thus minimizing the need for the credit card offers, old habits die hard and I’ve been able to upgrade free flights to business class tickets just by sticking with the plan.  

What is travel hacking?

Travel hacking is basically collecting frequent flyer miles without needing to fly.  As with everything else, there’s a labyrinth of information on how to achieve this online and the truth is, the more time you spend researching the idea the more intimidating it becomes.  That’s the main purpose for this post.  I’m far too lazy to manufacture my spending and the thought of calculating a financial arbitrage between the cost of points accumulation and money spent gives me a headache.  But that doesn’t mean I can’t continue this as a hobby utilizing my current spending habits and maximizing my return. All I need is a set of rules that helps me distinguish between a good offer and one that’s not right for me.

My rules

First and foremost, I pay my credit card bill in full each month.  I have never carried over a balance and have no intention of starting anytime soon.  This habit and the allure of miles can quickly snowball into a large mountain of debt, and no mattter how you slice it, points are never worth going into debt.
Second, I know what I spend each month on my credit card bill and I will not sign up for a promotional offer that does not fit my existing spending habits.  Chasing points is a dangerous way to justify an expense.  “I should totally buy this new TV, because this TV comes with Netflix and 25,000 bonus miles”.  I would think this way so it’s a rule.  Not gonna do that either.
Finally, I try to be realistic with how I would use my points.  When we lived in our condo, we were close to the Southwest Airlines airport; now that we’ve moved, we’re closer to the other airport with all the other miles.  I love Southwest and have achieved companion status through their credit card offers many times, but now when I see that offer pop up I let it go because it’s inconvenient.
These rules aren’t meant for everyone but they’re a common sense way to separate the offers that should be appealing to you and the ones that maybe shouldn’t.  When you read some of the travel blogs or message boards, the chase for the points is sometimes overshadowed by common sense.  One simple way to combat that is to exercise common sense.

What about credit score

This is the main reason people cite for not wanting to open multiple cards for the sign up bonus, but I’ve actually found the impact on my score to be negligible. Obviously monitor your score so you know how you’re being impacted personally but I open 3-4 new cards a year and my credit score has only gone up from when I first started playing this game.  It’s true that the credit card company’s inquiry into your credit will have a slight negative effect on your score but that is usually more than offset by the lower credit utilization ratio that the new credit from the additional card provides.

How do I get started?

If this is something you’re interested in doing more of and don’t know where to start, I would suggest reading and  We have no affiliation with either of those sites, I’m just a fan of their work and their transparency with credit card offers.  I would start with one card, get the bonus points and if it felt easy enough, try another.  If you enjoy it, you’ll eventually end up with 3 or 4 cards at a time and drive your spouse crazy (until you’re flying to Europe in first class).


  1. You are definitely the travel hacking guru of the physician community. Your results speak for themselves that it definitely can work and your rules are a must to live by. I put the majority of my expenses on credit cards and because of that accumulate a lot of points but have always opted them out for cash back (I too pay off my balance every month (actually I pay it fully 2x a month to coincide with my bi-monthly pay check).

    Is there an option for you to get cash for the points you receive and if so do you think the travel miles are worth more? I know I have the ability to either get a statement credit, travel, or buy merchandise with my points but hard to say which gives me the most bang for the points or perhaps they are indeed all equivalent and you can pick your poison.

    1. I tend to focus my spending on achieving bonus offers (like 100,000 Marriott points after $15,000 spent). These types of cards tend to not have a cash back option but if I used that money on a cash back card then even at 2% I would only get back $300. With the Marriott points I spent four nights at a JW Marriott resort costing $350 a night.

  2. Your spouse will be driven less crazy if you give very clear instructions (possibly via a wallet sized chart) of which credit card is supposed to be used during which dates and for what types of purchases. “Use card A for all grocery and restaurant purchases between March and May. Use card B for all gas purchases for the year 2015.” Just a helpful tip from a certain wife who just wanted to enjoy Italy for a couple of weeks…

  3. Hey Xrayvsn… the short answer is… you can only get cash back for flexible points: Chase Ultimate Rewards points, Citi Thank you points, and Amex membership rewards points. In general, you get 1 cent per point if redeemed with cash. If you have a premium card, you can get 1.25 cents per point (e.g. if you have Citi Premier or Chase Sapphire Preferred). If you have the Chase Sapphire Reserve card, then you get 1.5 cents per point. So as you can see, when you redeem for travel purchases, the points can be worth 25% or 50% more. But obviously, if you hate traveling, I would not redeem the points for travel just to get “maximum value”. Now… if you do enjoy traveling in a grand luxury… you can get really outsized value transferring these points to airline loyalty programs then redeeming them for premium J or F class (business or first class). By doing this it’s possible to get 10 cents per point of value. That’s assuming you value first class at face value.

    For example, I transferred UItimate rewards points, Thank you points, and Membership rewards points to Singapore Krisflyer (Singapore Airline’s loyalty program) to redeem two Singapore Suites class for ~150,000 points. Those seats can retail for $9,000 each. So we could have paid $18,000 for two first class suites or 150,000 points. In this case we redeemed for 12 cents per point.

    Hopefully this answers your question.

  4. I would say that it is easy nowadays to manufacture points, especially for high income individuals who pay estimated quarterly income taxes. That’s what I do at least.

    Every quarter I see an opportunity to earn a half million points and miles 🙂

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